w—u——— A SWDY OF THE SYNTHESSS AND REARRANGEMENT OF B-HYDRGXY ALKYL ARYL SULFBDES, HETEROCYCUC sumoss, ] AND PHENYL ETHERS Thesis Got the 009100 of M. 5.. NCHW STATE com Fmdarick J. McCarty 1953 1‘ _ ~r ‘ ”4‘, ‘ . .DI!»L'A A A STUD! 0? tar. 51373513 m: kmmmm or annex: 511.51. mm. 3:131:13, as: .aocrcuc saunas, mm mm. mam-3 23;! Frederick J..HcCIrty k TEL-518 mmumunoola cram Mu “Kuhn-3 M 801103. of figs-Multan Ind Appncd Science in prunl Minn-at. o! the neural-nu ta- thn chm at MEIER 0F 8613:3383 Bop-run“. at Chantry 1953 \ J) I C \ \f\ \.:3 - J' «I W's-$6" 'cmgtmwmwr Tho mthor mm» to express his sincere @pre-ciafigm ta Pmresmr R. 3. .331ng far his mane. and onec‘urfigizmant thwagmut tho course at this work. 4:1 :3 MM- ”wail: # “Mm em a»? :24: am fl- 3* G TABLE 0? CMQ‘fo". PAGE \‘ I“ . MEDWHIIC&OOIOOOIOO'00....OIQOQOIOOOQCIQOOO0.0100009000010000! to ”EIGHTH. ‘ ‘I 0.00-0.-00.00....-QOQOOIOOOIOOOOOOIOOIIOOOOOCIOOOOQDIOC. mmUSfl{*mCOOI-OOOOOOOOOOiDIOO.OOIIcOOOIIOOO0-.QOOOOOOOOOIOIGCIOO. EngmganCnootonouooooooo0000000000000.-OOOOOQOOOOQCOIooOOIOOO Eufifl 2 Mim‘nienyl) priantto.............u....u athjl 2" Adflziothienyl) buty‘ftu....nunoouu”no-u buthYl 2" I‘thiOthiCIvl) eruogogooaoao.oottooooOo-ro 1391.31 dehenoxgprOpionatO...u."nun-u...nun-o... 2:;t2g1-2-Th10phenylpl‘opkvnau.u..“noun."nun...” £33.le 2.“ ‘NfiImIWXWIJ What. 0 co 0 a o c o o O n o a o o o o o a O F.3m1'1 WWI:- pmpmnat.ooooocooooo0000coo-o...to. myl uwthOoo‘ntocIOOOOoOC-OO~O‘OIIOOOOOOII090.000.00IIOD 23: ‘tmomgm’1).1m'm900000000‘OUIOGOOOCOOOOO-I. ,. . “KY1 hflmogsgoooouoooooo-oooooooncco¢oooaa...~00.-0.000000 2 -tldofldew1)-1'bum.............o.o.nuno.on a A‘tl‘liOWEWl)‘1flflM-0oo-ooo--o.nowooo..o‘oo-vo 2?};3mn“l‘pwpm°lgog....o.oos000.coooboooocoiov000990 2.1.Etiapl‘mw1'1-pr ”101.000.000.00.ogc..qu..OOooo-cocoa. 2-(fidhimnphtnyl ‘l‘pmpmloooo.ououv0.oo0.0.0.0900... Jethiophanyl-l-pmplfnl....uu............u.u.uuu. flcthiot'xdenyl ‘2‘?”pm91ccouvouo-Otatt 000.000.0990 1 ’Mwund‘l Gavbutlrfll...“..,.................... 1 l-fihlflmyl)-2-pmflxncl.“noun...““no"....o 1 I”‘hi°fl@ht2¥1)‘2'wp‘mluuov10o09a....990000000~09. 1-phanafl-2-pmplm1..uu.u........o.u.uonuuu... 3‘ph‘3mn’4'pmfl‘mlgo.m-ooooooaono...-6¢oo:oouoooo-cooo Chlmfiklnll...u.u. coo-oooc-ooooonoon-.000-ao0000000000to lifld‘MOthWI-g‘a'WhIOWEMQ00-0... coo-taco... a 1 I «madam ~2~ohlaronutwd md 2-93 othiothionyl) d~chlorobutlm.......... ........ 00.0.... 009.000.0400 14,5 «no udmyl) ~2-chlsrapon't am and 2 «Mo- ”dw1)*l.ch1mpemm00000oo.unnoooooonocooooOQOOOQO Ifiahemv'Z‘OthmprMw..u..........u..”nun"... 1&“0’0’2‘fi390w pmp‘nflooQOooovo-'oo-uco-o-ono.ooo-DO lvmanwhiml).2-chlowmpanau..non-nun“... TABLE c9 CCNTELSTS «- Continued Pixel; :59 75 7B 8.; .5 .._1 Darn-@1415“:-.0..od¢-'IOOOoOavoono¢0lcovooOOO+OOllvov~OOOQOO a DMYmVfln.u-oc..o..o oculaoocouuoao-ooootoo-0.0.0-OQOOOOOOI 5W3}?! ....'. It!0.00.0.0...000.00.00.00-a.IQI.#iQOOOOCOIOU.OOQIDOv.00!!! '3? ~f'"'-'3.'! BIIJJOui‘ft‘IbY...Q.OQ.QO.. .u...‘lv‘ou..000..tong-GOOQcfltoIIODI00000 1mg .218 3 3 VIII 111 L151 W $131.35: P 14,6 .tmo 9.1.1231.) and 1wmowswn Ilkyl Alcohols . 1-99 mama-ml) and 1-04-mmhtw1) damn-o- DW'ow-ooqcocno§5000u0codoa‘Ocoo-OnoQ-Ooocoausoot-on PhflnflfiychlflfflpPOpIflfli.g.........a.....a-.-o-.acoo-onoo-ouo Ph.nfluypr°p‘n°1.occooocovo00..o...ouncesocl-ooooo-ooo.oooc w-rhiotmwl) ma 2M4W1tlvD-lnlky1 AIWBOQOOOO¢¢U6IO.OQCIOICOUIOOIQvQOOOOOOO00.0.6.0oon. WWW-96 .mumn um 163131-246 .mwwm) “1 M"OOOOOIO¢DO.OOo-a0uuovtooocoooooqcao00009-000 p-Imobmom orfldmwmxpmpmn um m Chlflrid'.0'OOIIDI'OOOIOODQOCOIOQOQC‘00"..‘03'...'..OII‘ 3,5431»: trobomom at flvTMothianylpropamll and flair Chln $‘.oocucc00.0...COOQOOOOOOOOO-OOQ.OOI.DQOoCCoOIOOD )JMtx-obomums °W «Whumpmpmh and their cnloriae...totostaictiOOOOtoooOQOOoioooVOOOIio-ocloa0'90 x s of 14,6 Mamiwa-Cumdm and 2. £WNWD‘1‘lllamdm.uouooo.oor.99.0.0.0...a. 1 gamma-mm: «,5 .mmmsmu um their Chlsrid..oflfl..0.OOQO00.06.09.060...’IOQOOOIOOQOVOCOOOOOO 35-33111;wa or (G-Thmumnylpntwn and mu- Chlorid.’.fi......0OO‘OD‘OOOOVQCU..IOOOCCQDOOOOOOO0...... IE 15 16 .17 22 23 2h 26 27 f2 .—‘...'-.-l‘-,£.i_,“~x.‘hI‘-'g' Du.» .1332. '43! mm; u» put duo-4t, anému chuiod ”tau-oh ha bum were. Wm: nth the obj." at elucidating the 1-01. of migrant-mg map. in Want and rommgmt auction, particularly those involving I ”can“: 13-min. In a tuna]. «mu, any m1: trmfam‘uonl um bu nun-and by tha emu-:1 «nation A-W-Cr-Orz '4‘ I. cum-9 1434.444 ‘ 3‘ mmamwwhmmmummuc,nmu on adj-um m, C... m: than «mutton 1: not intended a dearth. in any in)- tho two ”chain of tho “magnum, but nor-01y to “pr-cu acupunwmhmummmnmmnmgummm 1.th a ”Mt-tomcat reaction . 1h. gal-aunt); mophd m1.— 111 than nation. «a b. mm It runw- £\U 4 A 3‘ . i. ,i‘. ‘ ’ W ‘ t I I V zlc‘ II C\. a / \ "'-""':’ I t a C; *2‘ g. c; 1 "3‘ fi 0‘; I I \ I n . III m ammo. u.- pu-uupauoa or 2.1» mm; .33 (wig-marine z) in the Wt. 01’ 2 to yum um cyclic intamediau, II, which a: 09min: 714nm: the prodmt III. I?» parucipning m {inky ha of th- carp. mwuuhmnamm-d,st,watnybomnm ”~71 map. Th. inhuman. Knuth-n Momentum, tic-uni- ”menial“. mmmmauouormnnmmuaoumm demmndimuamtpmus. Inmrmwm mmotmmummmwmmmnmmmn mpuunmthmhuunbmuoimlmugongnn-I um. mmmmnmmmmumm “madam-of mm‘mmm mun flmmmWwMoWou-on. Thou Wanmwwmmnrm ..I a hat-crow H a hflmwmnt m,-§e}mm oflhor mpncnuur,tu.1um MLfl-nwmorJ-lewlmmdmnkflm. m,utm,othy1wn-pmpy1. Ann-ant) «mt tomato aux-m an arm or mum-ugh mdflontbl displace-ont- HW‘ Hutton than tho wax-owl group in alcohol. at w. Ibo" pmdwunfiuodbym. nupmmMmuthbunnmulmmwm ”mutual-«anon unwind, butomthnnmmmntdmor “MucumdtovhuIMh HISTORICAL n has ham ropes-Md menu: (2) that than twatomthyl-a- hydrant-apropyl «111m, ma.-ca.-s-cu(ca.)acapa, u mama with Wm unbrid- w ”plan the Mary WW by chlorine, on. m,-ca.~a«ca-ca.on 29L, c1m.-ca.-s-ca.ca«cn, 01 a "magnum mm u was l-cthyM—nhhn-n-wwyl «11160 . that this ”action my in a specific omph of a mu). plum.» a. mm by twain-nu um. «119'»:me “111d- M ethyl Wmmyl ammo. than Wanda was bound 11th hydro- ch10!!! aid or Many}. chloride mum in the am Met, Indy, W1 why! sulfide. CH. CH.CHr8-CEKZH,GH . 7,5511”? cafiafi-caficg-cn. “Mfg-CE. WMMothWImwumWomawmpfl mmfluumunmnormuowopflunmpfl «mm. ManmMdemMn-wmm Madonna. “#4?” "111a!" of momma. pmbably com Wtcynlu Wu. mumm. ca. 1 n-a-cwfi n CE I a» " -. .p/\,H min-s43 a-ca cfl—9 ’c’- C‘ .flcl . mares-cu. E a (33 mu. (J) um Macao. tar nah 1 mm 1:: m menu on the «law of m 20mm bum watchman acid and w chydmxg ml.- {MdvmmchdnmmnmhthIannuun-fl: namuonrmmm when]. mwmowmmmm m- u: tour mun m, u u sumac“. nu ma "mum; amrmxdoammmmummummummuhm mmwfln-CHM manila mmmmmmrflchmld Malt in g 91611.. woman ult us ca tutor-iodine. ‘ 33403).“ . KBr ._., [faraway] 3:" =3 314%.)“ ‘35-‘93: . Ln “tandem or Bannett'n cyclic 0112mm- 1cm inhuman“ to this no phi-out or m W1 why a halos“ “flaw-ulna. mm nun-martin». mauw‘wwmm cum 1: . «nu ct 9W (3) to account mm ohm-«d sunsets-ma W 1: «man Mum. «M muons. lath. W and: o: m cyan unaw- 1oz: Lam-«nu, "film in W1 2W1 mad. :- W with was-opp chloride, tin m. cam mum; in bank-n on an.» ado at tho mummumnmnornmarmmmm W. a 0 CB: /8\ ,5 ~23» smug-ca, . nagging 3”"‘3 lurk-bur, it u 00de that the two W cm” oapomia could occur tug-thu- u an wail-Mu mixture, in mun nu Us mums or 01th” at then in u pus-o In“ night b. «no diffloult a: impossible. m, in the can cited thun hr, the M-Mmyl mind“, 11‘ formed at all , In thumb" Malawian.” . Camila 1,2-4‘11fllq1 :mimchloroywpms , nitmgm analogs of the 3m company}... hm hen chumd (5) to undergo 3 Diana ms;- ”at involving tho mama.“ tor-anion at 01.291330 mm column. ”memoran-Wotmmmgmantinmmmganmiuithu I been pro-dbl. t9 effect ring “lawman 1-.th RWWtkwL—wrmniim Inning bun found to 195%qu ha InthyI-J-ohloropipwisfim (6) . y """‘¢-- [ g 092 I 1cm 1 [ -ca .1 a twain um !J 'c ,1? 0.1" i n 3:35 C cgz. 0.3. i 6.1!. 3. unm‘hubunmtucuwmtudnnu'MOWmfi cum- om, b“ an tho m ullplo a tu- mgml‘l), tin: iflwmn occurred mm o: ring alumna. tugboat or fibydnnblfio umwmo (1) cm: thionyl mama 1n WJM-n Wold 2mm»: ,h-cumm (Iv) . I 303 “*3” 1 m1 . .. ”9 (3-443! [car-scenic ] (1) (n) F / 3\ 1 / 8\ :33- ‘ifia in. am: «In...» ,1, ca ca . Ca ca 1 i :1; cm J < s)“ 3" L 0 (III) (I?) n a banana um thu-é—ohlmdA-dfihtamloham (n). u tor-o4 rum-cage. ta am the Manila Wanna ion intermediate (:11). The nausea-um” or an n-prop'yx mtm u the W1 nu ma boon W in tho roman a: mmmm—e-«me (3,9). mum at 415th aquarmthA-amm (xv) . afforded a 815 71.14 0! the con-owing 22qu «um. (v), as cum product. mm; mum. / 3 / 3 [can ‘9‘: fan ‘9‘: M . CB\. 8 ’mflfifil C34 8 [0368.98 (1") (Y) Rules, in MI ample, I tavern amuxgmmt of {he mrpmpyl ta tho mow]. “mm. did not W. 8.- abcanatlon. mm in tho 11mm (10,11) 11:61:11.0 tht't the imitation at the tummy! Wm to tho ”m1 mm, matured in open alum alkyd/9 «chlorosulfldu, may act. occur it an «71 group n attach-d M the m am. In ordn- fio detminn dmthar w- pronun- a: to £171 group vauld 9mm. arrange-ant, Mn :nd m (a) Mod the nation a: ZWWWWJ. phonyl amm- (n) flu: W1 chlorid- Wh "mud in the formation in 633 field of m ram-aged product, zoomro-o-propyl puma “1:111. (m) W of Z-ohlmimmyyl M1 mum. (VIII) . C11, 1.11. 01 (n) (m) (7111) Thu 1!. ha been 01mm that a 5111.va group does I“ prevent Martian «tundra-non, umuunxm,uuanm1wp1wodip phenom. at tho Waxy]. map with clawing. ‘ 0110 might 0mm that 111 um avg” analog: of tin ooawuma (linen-sad than, $110 mean an, witch been“ tho adamant-1:13 m, mid be «panic at puuoipttia; in tho mpmm Wont at an adjacent mom group. Amm mm 1131me (13) m www:u«,nhmuthocmmnnw1mh stunts-d to u:- was» “a. Thou «than hm conducted expat-wont. Involving tho column or, sawhzmuma-bmmtm (n) to an Wmthyl—i-butml (1m). 0 Q c :1 33 11011 :12.ng 11. 115‘ ' . . 1-1'11 , C CQCSMK :1: § CK Mfg—cal fife 3 ‘3‘. (n) _ (m) (XIII) PWon of tho adamant-1n; anthem]. group to (on the Marceau“ W103. m hn (XII) «.11: ”count. lot in migration. Ions at wwwmmmnmumnmnnmmyamw or 9139:»! nt the salt £11131]. substitu’md carbon, atom {allowing an attack by a 111111211110th: ion . The first 00me of 1.1110 investigamn use to £11111 mum: tnthetio sauna for tha preparation of u}? mpmmfia tibia}: mm ranked for a study of the! marrmgfimnt of amp-1131mm Wide: and 01.3mm. A Ema-mute march m man 1:1 11er to 2111:? raattisna which could be «5th to the pros-Jamaica of the dashed commmds md than which proved 1.43 ha 01' um: value 1‘»? the OWFu-Ill {mum-tic 3:31” V1.11 b1! discuaeari. Than adfltim of may” compounsfia to 913.1111. 1.1 Imam ta pmcom “car-ding to max-10121111071: r3111 11-. the presumes a: lulhu‘ (111), and than: constitute: 11 saw-1 method or synthesis or [413mm mum. mean and Kmhen‘m (12) hm 33531in this mathod to the pnpantinn of {Jr-hydro” M31 91101371 “11111: . cu, IE? ‘82 ' (ya HGCB . The ”mm 0! 1111. primary alcohol m ”minim! by treatment with Mm]. chloride using cum-ores In tho solvent... Tho written at 2-phmoxr1-propano1 by the reduction of d We pmpionlldohydl with hydrogen om pinning! ands has been ”parted by «no; and Britten (15) to gin .1 1m; field of 1.11. primary alcohol. ca ca, 8 Gauze-C110 232' i @w-cmuaoa m and in)»: (16) hm “pom the reaction of phenol and 6-11th van chlorate-tom 1n the presence or pots-31m iodide u n W to give good 311.111: 9: pm mu male-swam mm. MWmoWWdhl-pmbpmpmm Hfla-phmnM-pnpmx by hydrogen-ma at. 100 «no-pm puma-o hum-mum of think-100W“. 9 H ‘03 0 [C]. I: B . cl-cnrfiaca. “L” O .-c ' red. . “Mg-1:11 ""“""""’ carom ' Q ‘ 0° w ‘ fill.- W Ind been pm'lmly pup-rod only by use interaction at Wren-lawman“ and adh- phomddo (17). sun-1y , Ma and Kashmir. (12) pup.“ Swarm-11:05:11 phonyl mm- by 0 I111! alt-tau inept-0190:1110 remain of know). plum. mud. obtain“ 1m Indir- plural urnpfido and shim-com. o -3-ll| . 441.141 mg! Q " “$3.348. u-I-n’ Q ’ 433.011.“. 01! M (18) humumnmammmuwmm and. h w. prmm d a but. 1mm produces the mo mm” Alcohol. & CH 1- 3.03 B H-tCH @ . \. O/c . a” We .43 3 10 1100 tho reaction I: phonol- uth prepylono and: in m. mum. of uncou- m1».- nya-mao u upon-1...: (15) to gun madam-y 11901101 cm. hall (19) PM“ 1"le alcohol. by a mum of mm 11¢”:me (20)“obhinduu753m1dby mm a “into doom collation of .061. phenolic. cub tri- llthylm Chimhydrm . Pan-11 and In W ablation of ”dim ' may in mic}: m BMW 13 “pistol: 00111121. and tho ro- man-what! in imam-tar um and “battery‘s-1d. 3.! ' H R @431! o Cl-Cerlififififl :1: @‘M .43 ran-OH timer and £131“..er wind 3 1111111- 11110an to my.” 16 ohydromtkvl and Y-hwdnxypropyl 9W1 “111:!“ . -c «m G53 . Chewy-on lgfl" t) R. a, my an yup.“ m non-3pm; o( ndflfuphthanl W h and mm. GO " . mania: ____, “$011.43,“ mwmmummammdummmwm' “(mu-autuummmmpmaim. mmafiaw 45;?“ ”mm-1:11.11 Bonn.“ and 30111110103 (23) ”port a mac rotation for tbs pupa-«m up mum.- fl-hydroxytthyl 31111111. by adding nucleu- mwm to a column a: p-mhmn in a slight on“. of am potuuu hymn.» at. 60-70% and hosting . than use an 1 Into:- lath. Tho wax-ox: mm m converted to tho chloride by the action of pmmm pentaahloride . m.“ + 0143.43.43 % .“mfix 39‘» W4Hrflrcl W! and Salmon (2h) mus-0d Wmml—J-tmnml «111111. by a mum nation or J-tbuphnmuml and propylene abut-warm. .51 1 area-1:11, [7| 1 . . _. . 1&9 U‘H‘ s alcafig-ca, 13 on The nation. mu In” an» bun M We nanny 0911111!“ in a “W to 13on a control mthotu new for preparing the We: lulfldo and 0M alcohols. It m concluded that the nation. was: by ”a. tanning genord equation. would "-1111; 1nd to In Ina-Mum). mum“ or compounds which var. musical ta 3 Itudy of the WW remnant. I R 141-3 . x-ca-ca.-m ......., 14411.:11roa 05 GB In thew equations, rcpt-93min a plsm1,fl mwhfiwl 0r J-thiatvl grow, '1 is “that u uulfw az- onrgsn atom, I in an dkyl m and I 13 I halogen “an. 13 DI SCH $310}! ' flu direct “adulation of Imeptm and punch nu 1,2an m in but. solution to. considered to 1nd to In wand mm d tho avid-hymen Alleyl mum and 0th.". Arm-l . Cl—CH.-CH-R 4‘21" ;-rs-ca.-ca-a OH 02 The pennant: at a lid: tuition involving cpoxido ring tax-antic": and W "action with lore-pun to yield a W a! primary and “com-I7 alcohol. in. anew. This 1: 1n 110v of the report (18) mfcmtin opening of tha dkyl subatitutad epondo ring by ”NW8 and punch in tho mum at a basic utalyat to wane. pm Wary- noomn. ’ . the «adulation reaction m carried out both in aqueous dull Md 1: W udimitbondo caution with mpunbh finds. The nation in aqueou- alkali as tho advantag- of autumn; than prop-ru- tnlen or nudit- “head. Minion- and mom 8 Mat «an: isolation of tho product. 3101“ fussing Inn 56 to 86 percent were obtained by “trying out thc rotation in tea pea-cant Codi!- hydroxldo Colman nth the flatten. involving nmuptm axing tho high" yielda. The were uptu- dlu gm batter vaults than phenol than the ”action It. can-10d out in anabolic audit. nth-ado. In tho one attempt to prop!" “Wt-pupa»). 1:: audit: othaxtdo Iolntion, t onus. durable quantity of M in mound and a poor yield (202%) or product vaulted. L; This mtfind was or partimxlar “mugs in the «Mazatlan «flu-thin. nayhthol with pmm'lana clflmhyfirin beam" of tho inaclubflity of (éuthimaphthol 1n aqueou- alkali. In tho "scum «playing alcohol“ ”dim, sodium chlorida pmipitated and pmvidud a Icon- of quantity- tivnly estimating thc extent of the reaction. I» ought amen of chloroo mm m generally Med m1 tha hydronr alum. or other: um obtained an 0010210" liquid: by vmm Mill-titan. Th: mama winds: Ion eomrtod to thc catamaran; chloro- Iulfldu by nun- ot tho Dmm' rawtlan (22) using dry «blot-arm u a wlnnt. new. ringing rm $0 to 80 put- out an obtain“ by mum; the many mound 11th a alight one" of Why]. Wide Chick. had bean purified by distilling Ira! Muslin. followd by a accord distillation hum linseea all. It n- furthor found to be: admtageoun tomogacumntotdrymmltm numuMmtomnmlm mud. and Wan chloride. Two “tempt. m uric to mp1: thin e.- ‘ I at“: to the count-010:: or 1-9thme to l-thR-ehloro- propane but in mh instance the product gun I negauw tut tor chloride 10!: m mm with India. Elm, this martian no “amplilhod bycwWMthOMonmmidim givinzISSpu-oantyicldot n- chloracthtr. ”tap“ to prepare ponim md 3,5 dimmbem¢atu m M: Ma by tht postal ”and of mama; the cum-1:2. with th- Iocm- ultl of th- actdl 111 11001101 van mam. In contract, tho COW dorlntlnn of the ohlorocnlfidu Ian readily mm by thin "thou. 31: or an huh-on and smart: gamma: praparcd 1n the mottmurkhanmtbunprofiomlyropon udmodthur Mad pnpcttu m recorded in Talc: I, II and III. . 03.2 cu v0.33. ago 35. n . R93 «8m 3.. .8m .35 .5 .» .agazm Bu kg .§& «538 :3 has v3.23 . d‘llllu‘l on. .3 S . ga an! an o $83.53.. Engaged? Q Ya adma I ma Mmfi Sun :33 WSW” >57»: .uuwxwuu‘ aggzéadsfi?\z 3 I, We “WW 3.? £de $5.." \omdamfi onfiurhu ~39??Aa.§aofl?\ TH a Manna 2.2 dam.“ SR." alm\%fi 032m: ggfifififlgfiz a." Man mma .%n .3» 339.8 II“ .3853; 3334 .83. Aggmafia QT” 3 Ag «\Yu ma H mafia. 1-2. $0.33..” gun-sou 3... ha E a. ‘1‘1 1" {1| ‘1 2.»: NW? 83..” gauze asaaBao§VVQ§a§W I a. a . Wm." NW? 8..."; 33..” sfiQoofi Handmade §n3§?~u:2£§o§. \ YA ,.. a _ . 3.3 3.3 9%. a 5 «m3 Sumampu .ggafi?u.fiéodao§c Q .4 33 “mi $5." 433 Eur" I {comma dim: §§§Q?Ha33.\ I IQ” , . «35m 5. «db . a c mm; A: 5&3 3538 2.3. .335 a mm 1111‘ II 1 ‘1 «alumnus; §§§?A§uu 3A n5 gm?‘ I G A a mafia _ 17 .009“ an «6% a .33 madame.“ 3d 55m .3 v3.33 9 .3953 .Mnaxm 3&3 £063 9.3% bu Dianna .- an m . named.“ ”mam. H \onnéd H833 3839395231283?“ 3.0 3.» RAW“... .38 g.” 3.84 Ewoxofi-mw H83»; §§§§¥flé§33 8.0 m...» 3.6 £23 m... .a “mum.” amaomm ”825“ £125???” ‘1 1! I!“ ‘1‘] .32: .938 38» .293 . V . L it o kl n a an i.» 3.53.3.» Bingo . Waggdcd 1! 1m mu amalgamvah S4 Huwmfiwgrfi wmwfimofiugfihcfifi 8 mo HHH 3mg; 17 .oaew .3 30.83% a .83 “3.36.“ 36 afirfi .3 @333 n .333“ .33» 33 .590a 33m ha 3th a 11111 . A.“ ll. «‘1 8- mu nomad." 93$: a \omfiumd gfifio sun-mahoBEYHubnafinrm $6 3.» «n.4,... .33 3%..." “a; fifloxofiumw H833 gmfimfiodfioéfigfiawu 3.0 m3 dim fié $.84 «mum; flakomm Swim-u 335339.” 41‘ 1 ‘1 {III ‘1 Eu Jul-Hun 33m ovaofldu J L .. u an . A. p Ids-3h gunman . W uggdufid 1:: mm mm LL ‘ b Llr ll? IL? III“ 14‘ Icl! I‘J I141 .xnmoamvdh 93 auumcmmgfi wmfimofipgawcfifi 3 mo HHH Smut The 0211;; method preflmznly descrihm’; mzich was wailabla for the preparation of 2-06 ¢mgcryl)-1~prnpmcla inmlves! the addition of the Inn-ordain msfnrptm to 11134 alcohol in th’ pmanw a! Cultur. Arm . ca. - cunning £1" u-s-gfiicaga fiwever, mplication of this method united. In poor gum. and proved, u be of limited mantis 151m . “an J-thioyhmthiol in ”fluid 11th 3111). tic-31:01 for 3301406. of tmtyi-fmn- and forty-olght haul in the magma of sulfur, only : 27% yield a! 2-4/6 Manuanylfil- propmal m obtaineaf. The rasction m. also 12de out in I nitrogen ttmospl‘son ta prove-mt possible polymerization of mo ally]. define]. and Wide taxation from Jwtlzinphenutlsiol, but. £3315 rothi 111 only a slight more»: in yield. Finder the me reaction conditiomue cada- nthlzo} mm $9 add to «fiber 11131 alcohol or dbl ables-ids ad fib- th naruptw m mum along um: mfilfi-dinsphthyl dilnlflée. Ii would upper ma non drastic roam: condition ur- mum to torn. tha addition, such a, carrying out the martian in I (3318’ tubla. The pr‘epnrnion of EWWl-pma‘wl min; the nathoc’. unployed by samn and Button (15') a difficult ma um «aiming. It was mm: W to “Mt I magnum mm by the inter- when 0: phml and Mum-lmpnml, the lattnr elm-pound m prep-rod m tho int-rum 01’ W dioxide and prupylm following thu ma of Bristol m 3211. (25). ms omtuon mum in. «mud nut in Oman- llklli ml t1” 1n mpmpyl 0th.: containing new. pharmacies. using M111: primi- ot one 12:21::- and eight how: raspmtinla. 19 “than: tho chlorine of tin mus away-inn amt b: upland under than mm“ limo the product isolatefl from both reaction! III may want“ phunol. M. this point u m mam: that. ethn- tynthctu um mt b- douud in m to obtain tho dumd commands. After we auburn- ”An 1% m undone! um a 70:7 gem-1 mimetic sound maid be mmumcumammuna doctnlncmldthfihpnpm and m "emu: to th- Ilooholl by new: of 1131111: dumb We. (1) ”3:1 + Iain-cow .—_) main-60,2: w (2) Ar-B-gii-CO,::T _%_) gmiudznpn Th0 radiation M m human-.06 tint using nWla-Mhmlo ”but“ which m 0.011: prqmd by us ”thud of Kurd and Wu (:6). lay In W at tho yard «and or um and am (27) firth-Wotlthcnlnbhmpm, ad mw1auym~ phyla-19mm). m obtained. Q March-co.» £111.33.) G MKrC-Kfifirm Ammnmmmmmonmwmaum mxmwmutmwauamuaummumn, muummmmrormamumummm mm. Autumnal. ammo! material did an and” mumumummmummnuanm. ‘ 20 haw- am:- «a th- pawn). quowfiyttthlm W010, a in additional two Wands an mind. Thu «1171 WWW m prepared by running m Wu umlmmmnmmmmmmmu a' 5% field or the («ind «m. Ii» no an. decided to try us. than caudal-stun nation in mm“ 0041:: othondo ablation in dutch mmmnmw would: to gin swam-11.14 (715) at m1 twmmcuato. cu, .m 33.02:}: fi-crfit Q . circa—00.22! W (B . my a: u- oommun, 1mm "tried on 11361501101, had tho damage 9! pa. mgmmntmmmmuum mammmmu mannécmgmMmomdmmumm‘h-m‘ «mun. mnmuoumvucmmmwumumm Wm M I"! I- 721 11014 01’ 3MPWHW. ca. OR was @«HkOfi .._..._.L.§ 0.343143 .03 Etna Ingmar Mummammmwomuw m In. mum tad manly hemmed thou- mum. noun 0: 66 to 85 mt In” chain-d 1n the condensation nation involving Wfltbfizu wmmmmbmabmmummau net-nun "mun... Slightly nun.» yioldo "malted for both nation. than M in .1117th for the nemaptms. The 2-phmm1-propm1 21 W in um um: had I «may and nix-noun 1nd“ such varied midi-ably rm thou report-d by Suzhou and mum (15) to m cm (ac-pound) In tabla IV. flavour, thc bailing point. an: m vaulting pot» a: tin atmphthyuu-bmu during“; or w. W m in good mac-m. who density and "fr-cu" inch: of a» 2M.» mpmummmwhmmmfiummmlé ping-zapmpml u n th- an vhnn th- plvoiu‘l nonnat- o: thc mow 1mm, Madam-sprawl pml «1:140 and adamm prowl plum sumac m mind (12). a.» mm mm mu. no. map-Snot dubshunmmdbymau rotation-um ulod i: mm awn-1mm}. and they mun Md «mm mm mar: bathtub. huovuzhau Inaugu- “unauth- mmmduthodotmmm, n ummmmphymdm M obtain-d for ”hound-prom in thin min-manna nu ma "11m: than thou ”pox-toe! by Sexton and 81'1““ ma Mu ”madly tron tbs punt“). mutant! of. it: w, I-Qhomflbz-vpmplml. “hath-r, in th- an". at W work, 01w an mom- ma 0mm utmwwunmpmd udouootthurphydcapnpu- Mama-durmuvmu. m amm- proplfld by the to cup Iyuthom demand show fin Maud tub m1 mm. in order to domain. a: murmur! Inn occur It»: the Imitavl m m "placed by cumin. Whoa l-(fl—thiothiwflw III manta-:1 to the nan-Wm rotation ' condition, CE Wig-(1330i! fi.‘ U-fl-Cfifgg-CH. 8 8 22 .fidgafinaaaofioakfihg. mac.» 8mm.” E c.5533 non—ms .§§2a*?a omTfl. 38.." 233 IQQomEa «gamma Hana???§m§ fig. 0 824 . .5 05mm” 33% u .nBfiSPTREEarw 3.15 «~84 Run..." 5 aoafiéfi . “Emma gagunauafiunu cane-cog: mun. mmn .a. a nick Eunice mo .5 5 32w .3 Bag 34 Eumagfi afimomfimofifi 23 .omgu :5 «Bag 35 «o afifi 338 2a a 1111‘“? i ‘1‘ ' moo ”M44“ 343 \omoacnw." amigo -nflgdsqmfiagodfil gum is moo ma. 2 3.3 an.“ «3.? >219 mamxmau H§fi§asfiéwd§d3umx I «0.3 I ma My“ 8.5 934 SR; \oafiuufi manna-o gfcfigsafig%>& mm: and." 284 $.me I (ongfi $st H§QEFTA§§dfiu\Y~ mu . llll'l rlrbL still 38.. 6.3.... man as :2 gnu _ .aneso .33» .333“ mm 1|!" j! .1111 ‘1 3.3-me «a 3%ch gavagfigaQI g g§§?\z kg.“ lad 2.5 3.3" 4%: Ram.“ >339 nfianaugfiimwo-«fig I3. 8.? an? 8.04.." am." >318" ufiasuau SaigoVV-ugm l man. an: .32 33 an? 5.3.3 .33...» £52 3.3.3... 33 .84: mid." can \nmflamd nope-an.» gigv‘xgu 1'41 1 1|J|I J‘lul mm. m? a.» all _ Ill-8 3 g Mfltuig Héafigggagg §?\I§ M. an. m- mm: m u» phylifill pmporuu (nu um. I!) a: tin chloro- nirido W by it» nnlagoul fur-amen: or 1-W-thiolhicmrlhia- '0me Idtb thiom'l chlorido .. U «urea-cu, 3051. U Magma I OH c—n—n—g ‘ ‘ c1 . a 5 Both product. at the chow nwtiam gm .- moot calm: cumu- (29) only!“ 101' tho tannin (193.5361. To pron its. identity of tho two shim-niacin, both m p-nitro Ind 3,5 dinitrobmom daunting, m 301.- VII ma VIII, m mm by a modification 91 the gown mm or run» (12). The ”Jun; points a: the dorintivu from tho hwuummu maSO-Somcmnodapruoim at tho melting point. Fax-thorium the "lung point. and mind melting mm at the dmminl prcpmd rm tho chlorides 1nd tro- 1-W~wio- mud-worm! an identical men proud tho chloride. to b. a: flu in. mm ll flu nacho} «whining inc/éa-Mdrov—n-propyl «a. chain. mm on ibc ban or mung point «ma, 1: ha bun mm. mm that 24 fl-WWD-l-mpuol upon treatment with thionyl chi-ride do“ rut-nap to produce 14,6 undothianylhi-eblbrapropm. flu magnum roam in Illa carried out using pyridine a a “him instead of chloroform and reunited in a 26:3 yield at tho cum-o- nflido finial; likoliu proud ‘0 be identical with the nmmgod Wan mm in china-emu. ca. 0W3.“ Grill. a WHO]. CCIEH. ‘ 3‘ . $561. a 530.030). 26 33w 3 . 3 £35: omé S ammus 3 . 3 Es owém 3 031$ avg-mafia Saganfigéao we...» 3 omwém acaumnmio qfi§§?2a?§n \ I 3 .3” moonmaucuo aifiuuwofigfius: VI 3 cannon? ”00.32%". 337333»? Q7“ any .u .u finish go .9331 n a Qamfimfiamié a E. 3.“.Emvnmwmmuomumnm mo .5 awgu 83¢. 93 33«§§%\ 8 Eaégmomhz E San £3.33!— unafimgfi 5» P mob-mam a .95an 3 4 as g mmém Q 0313 «moaumaumaa o .098 namogdflxgdganflfit \ vi." no 93:3 amueuwamxu agnazaéfigs? \ I 3 omgw nuooumamxo 3:73.333? KY.“ Au .8» .Eu no 8855mm m4 AQBTmtmuuzu Rs 39.8 on?! «N I“ 333 SE m5 flfiéoggua My? mg‘ogagfln an M3,; Similarly, 2-(f3'~¢htonqphtuyi)-1-prop:nol val found to rtlrrlaga m 14/5 «thumphtwn-zaommpmpm 1a 77% mm m mated with thingy)» cum in ozfim‘afom. Tim. nmmgmsnt did occur us again outdbliofiad by‘c cumpariaon.of thy 3,5od1nitrobanzoate darivativat or the two 1.3mm ileum}: 1-4/5 ofldonaphtZ-gl)-2-1)ropaml uni 2-96 -tld.o- nuphva-l-propml In}: that am derivatives at tho omen-0mm pu- parod trul»‘hn rvlrrangamcnt ronctdon; lao‘Tiblo 1!. ‘L8 in ‘hn'privioul can. fxnixnémacltinzgpoint of tho activativu prupcrod Iran the chloro- mm» with tho u» den-mun Mm m 14 flmxzomuqn4~ Ill-0pm no mt dam-and, um proving an mama". to be Mammal. ca. ' a “3.03.43 cml. - .3423 1:343. . + 30:1, --------> 01 .33. + m It in. not potltblo to analyse tho aarivntivea {ran tho iaanarie alcohaln by tunnel: of ma. 3m due to their “001:1th in mm acid- interwniztnrul and thnir qppurent alou’reactivity'vith‘bruufinn. A carbonp mdrogm mam. nu ”do a: the Maths: and gm good remn- con- plrod ‘6 tbs allcnlltod‘Valnnl. u a: remit of mo difficulty encountered in ”placing tho hydroxy group or 1-phmoxrR-prop ml with aldnrina in cmmtom , the Ottéiapt to run-mg. 2-phonouv-1-propmol m atria; out in pyridine . The ra- netion.una asrriod on} in tho Ian: manna: as has baan daacribad tar tho Gamma of lwhwow-pmpaml $0 kphanoxy-Z-cMQreprcpm-a . In W instances attempt. to pflpwe the p-nitro ar 3 ,S‘dimtro’wmam 29 .3338 ugh-a..— 05 3 fig I ill 11 1414‘ 0333 3 ¢ 3 933a aim a. .5ng uncomaus u aifiaflofl?unfihfia&aaflan V Y” .o 3.». 84 m3“ 3.9x. ofign «fiaimauu “game“??fibggoggw I 3 mo; .86 03m. firm $43.: 318330 a§a89a.nb§&§§nQ I 7 I14 1] 111.1 23. 6.38 323 6.38 m o .Hm «gnu no smofififiagn an a 395., . ii 111 Iil! 1‘" I Ulla In“; «.3. acummohmo-Wmsx «Avg 3: GU. uMJIQmoMmu-mkiquv.‘ mu 5 3356 mm E mug Smfimoagwfiafiw \8 mmfigmmagflunun an .33..“ 33 m: the 0321031395 wen manner-Al. Ema tho usual method of com- pariton of the cllari’lm from £13 numeric; alcohols 38C not availdzla. i. carton-lawman Inalflil of tha tun anon-fie: gm remit: for cmdson .3216}: mm mpmxhuteh a percent Nah in both 613893. 301:1} on the tan-$10 of 3911361031 constants, «c Tabla 11x, 11. Wald appea- that am zaphenonn-lopropaml «11:! not ram-4‘s since the chlorizfa prupu‘od In it had pig/sisal properties Which were in better Immant with. those reported. for Rwlzemgml-ohlompl‘apm (25) than than dammed for lwiwrwv-Q-ohloropropum. thinner, thin «mama :- In: 66:10le am. tho amt puritj of tbs phounycmoridao in in Men, and it add be mam-7 to tint obtain Manna of we Md” in order to pron or disprm the nmmgmnfi oomlmnly. Th. p-nitrobemox‘m at an-l-pmpmol and l-npknmxar-2-9mptnol were both obtained in mm yield: sad their ”lung points are reported in Tibia IV. '31:. rmangament of 24K fiflxiofliiamdbléuwxol slim; tré: fitted with 1.1.10qu cum-139 resulmd in tho tomm?103 at a nixmru 01' the tin pouibla isomeric emu», 14 fl-naotmwlm-cmtm and 2- ( flammmaH-anmmm . CH, 32:, ~ Fm ca, CH. 4 (3.51“ + (71" (9-3423. £3.81 UM“ «- 08,03 . S nag? far faint, unau- man 14,6 dhumuer-flobutml um «um um. Way]. man, I unma- W round hiring uncut gamma phylical Mu, m Tabl- I. .nuauuapuAgexnaaainumn oma.bpmxzadvgm - -.mH mm.m~ 3.3 3.3 3.3. E m.o €32" mam.” >373 Ffimflmau 853%??53‘1 B. . aging? VJ..." , as We mama.” Ram...“ \ofidéd 333.3 g»§m€ofl?~cfi?¢dfi§? Mina 33 23%;?“- figfioda..n\ TM a m. o meow.” NF...“ \oooaém 5&3an Egouaafimfidzéaumvx Ta 3. 3 .33333-2333337 b5.” 5.. m6 @634 am...” \o§&m 8.533 gnagfiiflnfigaad? .ox Ta 3. gau.»§~?~o 93.33? “KY." [‘1‘ dais» 3398 figmuuhé in Enigma um flxgqomfimu-Hsamfige: \Yu afi. fimafifiguvaflghx? V39." 8 3353. N ”Emma 32 HP DOS-CWfll 31:3 1 7 3 + 11 431-21! 4'3. <[§1.J. 2;. a ll |' 3 (iii “{us 9 WfiHCH, I! D C1 8 Th. tact tint that product: no datum: at the imam: chleria’au Ia! Mthliliwd by Wiring th! Jmmfimoato darlvnfivu, m Tabla n, of tho «a fixture. md taking I mixed mum; pint of thou «mauve. with m 3,5-d1n1urmoau Wand mm 1-96 oWyl) mm. m. darinum W m tho ho suma- amm- «oh had a ”lung pom at 103-105°c m a 50—50 Axum or up he had tho m melting point “an prom tho autumn u be identical. mu 1. to be wanted, lines the pontulatad internal“. «1103mm 1on “eh tor-O during the nonunion of the alcohol: to the 0111me wild be an m ngmmu at am doom). 1m wand. m: 3541mm- bount- pnpma mu l-w mmmmkz-buem m 3 making pom. a: lab-105% and a 50-50 nature or m1. derivative um either or we claim”. Iran fin «shim-id. unturn- 1-0de in a amnion of the mung pout to 96-98%. 1. may a: the Tablo n: ma tn. sexing pout mmrwxmuuuthnmhammumnmmum mm" from tht shim-ids- an om: WA; #1 705 of. the w "mead unload. and 303 or an rearranged cum-m. Th. m of. Mntin- mm salt. a 103.10%: can-ma to m poniblo paint. on flu slung pom mu, c and 0'. mm (-0 mutant! tho halting pom o: the pun Jfidmmbemuto o: 24 flauziotmml).1~mm1 .§.§-§2§3§0 .gcvahaggun .gagauahagu 3. aging“? as. 3335-33 33.33.. “3%: a 36+ Aug-blag? an.» own.» 0333 .533qu §2§\3 3 «M» n2.» $.73" {Jana—ac «Ilia-£85533.» 1 133 ofio use v. o a. i 1 I 1 J n 1 , u w n m w u; . . . :1: all _ ign H [r 1 t mug r in Egg .1 A , J1; _ gluon? xiii Raga-nag \8 gnu—Bahia u(b)wummuupm¢mm3mw Worm-(AWN. nun-macro. wawuwucmmmmuth)wm ammummnmmmmmm.muumw um.m4honu1~mmu. m,uctwu “mm-«mm,mwuuammmum .mummmpmmmwmummwm .Wfl‘bfllfiam. mmmmfldflh mm,uu«mumumuwwm. Hutu. mm)wmmumummmmuumm, ammum. ummcmumu- umwmuumwmmmum Withhludhuut‘hn. WMmWMhMoM,8 (AW-WuHflW-Iwm Mduwma. mm-«wmuu-m Mumumcmmwuwum Um?" , " Wfif" . , F, .61“ «- ; UK“, ' " 1:: m ' 4 WW! Um I mummumzwmm,mrohm,w mamawwmdmuwm 35 .§.§.I«§l§§a§:R-§o .833 «338.5 Yugo.— .gflggékgd an“ "era a: no; .5» w.” 8;. MD“ a... mam“ 2.5.. .34: «.2. . z; 2.. ., a... 8» on... 3.4 49““ $3 .915 3.333%? 3. 3,313.3? “Sh-A3. Svgomoom C 3. Egg? nag-«3.1. u .lfiufiflwfluvfigfi gunk-«flog: G a-ooaauauau 155958.??th .931. b?“ B- 8392. garngaflaivun a. mm“ good ‘ omit «nae-mama» gnaw-3313 M...“ £0 u cant afionnamau ggvfiéogoggnu A. 3E ”.33 83.. ”.38 was... .288 as. .938 u u . a.» 99.5. no 88839328 n n: i E5 1 u. 3.3. gagg 8- 5.815.799 9538 a! a! 3455ng gogn Hug 36 denial. can that um (79-61%) , and a auburn or than “I: «dunno yam a 79-81% man was um an m amnnm m mama Ind a: mum that th. tn chief“. nixturu rm- which they «or. pre- put-d m but bun manual. This in confined by tbs physical proportion of the two clam-id. autumn uhioh are identical within the 11:1“ a: Watt]. mg m Tabl- I. u in tin media; can, tho tor-stun 01' identical Mamas“ “110nm: hm during the amnion 01' the alcohol! to tho ehlnrldu mounts for tho identity of th- chlortdu aim-l obtdmd. A may of table 111 and an mm; point m, Ham II, for tho niacin“ indium flat tha nature um I» at approximately 50.50 in mum, cmponding to pom 6' on tho m'Ipb. Pom- (a) and (b) ram-um thl pur- 3,5-din1trobamuu «drains of 2-( «‘7 ofidoth1my1)d-pmm1 and 14 (3 dthiothiom’l) mm}. respectively. It. on: I» um am. am appmmfi 50-50 m ctpuro (u) and (b) bu {waning point. or 80-532“ (dew mum-11:) mick earl-”pond: rmmly with an 19-51 mung paint of tho nixtm 1n caution, indicates: by point C' an the m. Further, an muo- a; 01W (1») u- (‘0) w (a) an»: In amnion or tho alumna-immutammmum not-mm. at. 50-50 owe-Anon. All of the dam-inn»: m a corn“ tux-1311: for m unfur- and th- in dorintina prapmd {m the ammo mommmmcfifi, m s gxmzmumenmu In: good W um tho calculated when, on mm 111. the 90-11me m coma-nod that the derivative. obtained rain thu cum (up. 79-82!) light In We tom or the derivative! Wand tro- TEMPERATURE —-—> FIGI MELTING POINT cums; [3C IZC ‘ H5 ‘Y' I C C J, J ICC- 4" qg AL 90 4v w“ 0/ ‘I‘N ‘ {w ICC}? /0 C 0’4 Pv 8’ TI ON N77 ET 9 \\°”' , 1‘ ' --.- _. n _ w- 0.2: ‘- h—D’LH’CHOC 4r: ‘ i 5 CF Th-£; Q3 1 M [57 o .2 =0 ,3 i-[‘(’/‘\ -—) TEMPE‘F’ATUPE no ICC '45 KK “\~ .\\ 90 4" \\.. \‘x I \ C ’ // 83 .. \r/ 73 4* (z 3 4 a . (I; @092 0/0 COMPOSITION 05/9 “A- »— 7W a”, U9 -H (:ch c-(q 71' PM 9 N01. : " S'CHa‘CH“h-P~ ”a 4 [gr Ab ‘i é: O I?” If" FIGJI f‘v’WELT/NG POM’T CURVE the alcohol. (mp. 9&4?) . The «isthmus maxim I: 79-81, were nelted, I110!“ to cool 1.11:3 WI, melted Ind tha We” repute-d. In each case tho halting point. was 79-81" and the" m no Mutton of a change to the: higher melting point. Mmmore, ti): afimuommm «tinting papa-ad from the product obtained {mm the mum of 24 {9 ~wmmny1)-1-pemm1 um magma chlorida, m hydrolyzed with alcoholic potuh, and the 3-an 9;: alcohol: uwreby 1901““ 1mm oomrtaé back to the )Mnitrobmoam by the mil method of preparing the darintinu from tho Alcohols. Thu uniting point at this din-111M” was .8143" and when mind with the 432-131;:er derivative waiting fl. 7MP , than Va. m deprea anion of £3. uniting point. 9 a 1;) 31? 33.71345?!“ w 1-2 ~Thiothie 1 o m and fltlryl 2-( ,6 Abdomianyl) prepidnato ca, USCG HQ ‘3 .il’ 8 Into t 300 :31 um. mind flak fitted um: a “in", "flux condemn Ind drapping hmml 1m placed 120 .1 of Ibloluu “howl. Tho nu: «a «com in an 1o. bath and 6.9 c (0.30 ml.) or not-1110 sodiu- m added while aux-ring. Altar tho sodiu- had dis-01nd, 314.8 g (0 .30 :01.) of J-thiophemthiol m «kind rnpidlw and din-in; m manna-d a half hour. The «Elation m then heated to its roan tupmgm md 60 g (0.)) .01.) or ethyl o( -brmpropionm m Idfied dropuu to the Curved caution in I one hour mind. Pmipitauon 0! ”din bromid- omcd an.» the first I" drop! of the 11310 «to:- had bun added. relieving tho addition a! the halo outer the :3qu .- nflmd gantly for two hours to caplet. the reaction. The “action W In then cooled md filtered to ream “1t. Additional "11'. was rumored by cvaporaung nacho]. until (unsolved “It tgain began pracipi-v fitting, 11101111; the 001111.101: to cool Ind filtering u “cant! time. The filtrate m taken up in 3:30 :1 of other, mhad first with 50 ll of m, than with “a 50 :1 portion- a! a 5% sodium hym-oxide solution, 1:]. ma finally with 50 I1 0! rotor. After drying tho othor oclution with mama codin- mm. cool-night, and removal of tho other, the product woo diotiilod through o non Vigroux calm under noun: to yiold his I (0.20 mic, 69%) of on ohoot color-loco liquid booing o ploooont odor. Ito physio-:1 coutonto rot-o: b.p. 115-116°/1 In; n55 1.55m; :12; 1.1615. Win at tho compound for tulfido sulfur (2-9) gavo tho (outrun: result“ Colc'd. for 0,111,930.: 8, No.81. Found: 8, H.331 131.83. In o «cowl proporotion of tho ”no cucpmmd , 250 nl of obooluto alcohol on hootod with 13 .8 a (3.520 nclo) or metallic ocdim. To thin «lotion of oodim othcxido ooro carried 69.6 I (0.60 mic) o! j-thio- 9mm.“ and 127 g (o .10 m1.) of othyl Okc’u'ooopropianoto. mar maul of Indian hmnido ond ccncontroticn of tho obcvo roution mix- turo, tho product no ortroctod with other, voohod with tutor and 5'}; ocdiu twdrcxido caution, Mod and room:- diotinod. Tho yiold of othyl a4 ,6 othictMonyl) propionoto m m o (0.92 mole: , 85%) . Ito phyoicoi canotonto om: b.p. 132-13h°/S no; cg; 1.51410. In o third prop-rout»: of otbyl 24,4dthicthiony1) pmpionoto, o oclntion of 6.9 3 (0.30 solo) at oodiuo in 150 I]. of oboolnto olcchcl no trootod with 3h.8 g (9.30 Iolo) of Jothicphonothicl follow by tho addition of 61.5 g (0.35 I010) c! othyldobmooprcpionoto. Tho nation no Ion-1m: out and tho prodmt ioclotod oo VIII dcocribod obovo to yiold 5b.; 3 (0.25 oclo, 81:32) of o put-o motoriol which bod o boiling point “113-11571“. Ethyl 24 fl-uuotmergi) butyroto Uoing tho opp-rota ond procmiuro doocribod obovo, 16 g (0.70 polo) o! ootollio oodim ooro diooolvod in 353 m1 of obooluto othonol Ind 81 g (0.70 oolo) o: J-thiOpbonothiol was «tied to tho taxation. um- o‘tirring tor tutoon oinutoo, lbs 3 (0.71: mlo) a: othyIOk-bronobutyroto ooo oddocl lion}; to tho hot oolution. Tho oixturo woo ronuxod gantly for an hour cud. o bolt, ooolod and filtorod to remove the inorganic colt. Tho oodico bromide woo vowed with other ond otter drying it nigh-d 65 o (90:: at tho thooreticol amount) . rm filtrate woo oonoan- trotod to 150 I1, token up in )00 ll of other, and washed with too 50.111 porticno of Si ooiim hydroxido ocluticn and cm 100 mi portion of outer. Mtor mm; with oodim oulfoto, and removing tho other, tho product no voctnol diotillod through o cool]. Yigroux column to yield 133 z (0.58 solo, 83%) of on moot oolorlooo liquid having o plenum odor. Ito ptwoiool oonotonto oorot hp. 115-11806/0 .5 no (oil both t-smporotnro loo-170%), 1155 1.53573 :32; 1.3469. Analysio of tho cmxmd for Culti-io mint:- (2?) gm tho following results: Colo'd. rm- eunusaou 5, 13.91. Found! 3, H.053 LL32. L3 Btlvl 2-(K1’ -thiothiony1) valoroto ca, (:3, WH‘CO'UY By tannin} tho oosso genera procohro dioouoood obovo, 23 g (1.0 .01.) o: oodiuo m diooolvod in :50 ml or obooluto oloobol, out? 116 g (1.0 unit) at J‘tbioPheno‘thiol m added to tho hot mum othozido oolntion. POW; tho addition of tho K-m‘cnovoloroto out: o rofhu poriod or two no can halt houro, tho oolotion no cooled, tutor“ Ind tho tilts-Ito oomontrotod to 15?) a]... Tho orodo product no ootroctod with othor, mood one! driod. Attor- rwovol of tho othor, tho ootor no diotillod moor rodoood pmonro in o lull ”grout «1.1:. A form at 25 g of othyl °<~brooovoloroto woo rocovorod boiling ot SS‘C/Dj n. Tho undoing ootoriol woo oiotinod ooing on oil bath (Wotm, ITS-190°C) ond beam: .1: no-122°c/o.s no to yiold 160 g (0.66 Duo, 66%) of poro product. Tho poro ootor ”‘30-'51 o plouont odor and o light roller color. Ito «sanity and icon or titration ooro oo follow!” a? 1.5293; :1“ 1.1202. Analyoio of the mom for ouJIido Donor (29) gm tho following rooultu 'Ooicu. for 0,411,535)“ 5, 13.1.1. Found: 5, 13.28; 13.22. Etlvl 2-phonoJQ-prcpionoto 53: @mu-cmm o \ “A 'l‘no "no toehniquo ow “plow-=1 as damribed previously for the Maegan tida ootoro. A gamut“ 2.7 g (—3 .12 uncle), of oodlm woo dimlvod in 50 m1 of oblolut-s ethoml our! 10.9 g (0.12 mole) 0f phenol woo oddod to tho hot. solution. The mutant was! nine-:1 for tmnty omutoo to Mount caploto formation of ooeiiun phoamddo ond than 23.8 g (3.13 molo) at any]. d—bmmpmpionoae was aided dmpvioe to tho oodimu phanoxido oolutlon. Pmifitation of oodim mum did not become opporunt until most or the oL-halo eater bod bur-m o-suisd. The mixture was refluxed for em hour, cooled and filtered to renew sodium bromide. The filtrsto was taken up 1:: owner on: wash-3;: With tlmae 30 :1 portions of 5:5 oodim hyfiroxido oolutian and ones with vat-3r. After Illowing tho otlmr solution to stand in contact with oxfiqdmus ”dial “Bate overnight, ‘bo othor woo mné and tho "skim product mun“. .& roll form of 2 g woo collected thick boiled war I brood rongo, 80.120°/6 on. Tue moining moteriol m diotilled and yielded 11.: g (3.06 halo, 50:3) 0: ooter having o ploaaoan‘t odor. It Wood tho following physical constants: b.p. 1?O-122°/$ m; 1135 1.1032. flu pmimly ”period (1'3) boiling point for mu outer woo WI!» an. L oooond proporouoo of: tho oatm- uao carried out unam- nightly cur-rm commas. rm wont-11:1, 11.8 g (0.52 non), of ocdiun mo Mod to 225 31 of admin“ ow}. denial, tollovod by mo oddition ow: mm; of £35 I (0.52 min) or phonol to tho locum «1mm Column, out-ring bong oontinmod for on oddiuoml bolt hour otter ”so out“ of tho M1. on. 5.1m” of ”cum phonyloto woo boot“! to ’“T‘fii' _ ..,-. _.--_xf‘ 9"” W . . ‘ ' ’fl In.“ -a. LS 1t. folio; toporotnro ond 107 8 (0 .59 3010) of d-holo uter odded olooly. “to! “plot“; tho oddities: of ootor tho reaction nixturo no "am for tour ond o bolt hem-o. Thooixtnro no then cooled, mum, ma. on! driod 1n the mo unnor oo tho tint ran. Follow- in: wool of tho othor, tho input-o product no diotillod to yiold 65.5 o (0.31: oolo, 65.15) at tho pun «up. Tho oupound boilod a. 188-130°fl.0 - (on both tmporoturo 165-17OOC) . EWM-Mphouylpmpionoto ca, G’s-Cil-COfii‘ Tho ”Moro mood In. tho oooo ‘oo thot «ployod in tho preview propcotiono. A malty o: 2.90 x (0.13 I010) or oodiu no din-01nd to U 11 o! obooluto othoml, out 11.1 g (0.13 ooh) of thiaphonol no and to tho caution. tho «mum mutton ooo than cox-r106 out by odd“; 29 g (0.16 Io1o) of ottvl O(-bronopr0pionoto olooly while tho m no bun; out-rod. Tho ropid roootion moultod in tho Motl‘ mutton o: nu- was «to on. volition a: hoot. tone-m momma». d-holoootor, thouxtutooooronnndgontlytor o. hoe, thou who, ad 1‘11th to rm tho mtg-nu oolt. Tho mono-m dtooohoduISOdholother unannouncum, tumult-111130"! lurid“ oodin woto. n;- othorvoo mood 'hyuotnhttooudthoyonooonmotmgvoodtotuhdmdorndmed prooouro. flu-o an 3 [of 1m tollmuodby 20 g (0.09m1o, 1M Ms riold) or o “may yellow, olou- oil which boiled ot 11971) no. Tho ton-Bun index of tho “pound on oloo dotmiuod, 13:0 1.5323. Ito prououoly romrtod (31) boiling pout too b.p. 139°llh no. A ooconit‘: proporotion at tho ootor no corded out by o Inclination of tho gonorol commotion rooction mood proviouoly, with o maltont doorouo in tho 11.14. to. wontlty, 3 g (0.13 lolo), or mm- m plocod uoW,BOOolflukvtuchcontomalOOIlo£onhydrono nlono. Tho {look woo rum with o roan condonoor, flapping m1, of!!! on “(Moat who ours-or. v-Tho (look on hootod to Iolt tho lot-1110 udlumdotlmdvimulywothoqlonomonmdtomlolwly. Tho and; poo-loud notolnc oodim on than trootod oath 111.1 8 (33.13 Iolo) of thlopboaol ond mod oorotully to oomphto tho oolt torootian it tho tbiophonol. To thio m added, {run I dropping tumol, 27 8 (0.15 uolo) o: my). o< .m-opmpimu ond tho m was refluxed gently for than an! ono bolt ham. Tho oolution woo then cooled and tho oom- ma. mood by filtration. A quontity at 100 do: othor woo oddod to tho Introto ond tho solution on woohod with too '30 I1 portion of 5% Iodin- hydroxido oolutiou ond m SO :1 fiortion of rotor fellovod by drying "or anhydrono oodiu oulfoto. Tho othor and xylem ooro rouovod by diotlllotion out! the yollco 011 mowing vol (11an tumor m to an 15.7 o (0.07 non, .85) a: on olnoot colorlooo e11 honing ot uo-lhs'm loo. Tho prochmt m rodiotlllod oad bound at. WSW/11 on. Ito reportod boiling point lo 139”“: m (31). Andyoio at tho product for mlfido oulfur (2?) am the following rooultoo emu. tor c,‘;n“o.sa s, 15.2h. round: a, 15.03; 15.13. ‘ M Elflrgd. 2-( (6 flzhnqnhthyl) propionoto cu, m 44040.3: Into o 500 nl throo nookod nook tittod with o otirror, rotlu oondonoor ond «trapping tum]. voro ploood 250 ll of onhydrouo othmol (Wino-0mm olloy) ond32¢(0.20-01o) “flu-thia- nophthnl Ihioh loo pmiouly embed in o oortor. vaioion no oodo to bubblo dry nitrcgon goo through tho notation oixtm'o Ind oftor W tuthooyot-rortonoiontoo, unoinmmmodtodooolootho fl-thinnophthol. o oolution of oodiul otholldo no proporod. by dio- oolving 8.6 g (0.20 solo) of oodino in 100 :1 of oboolnto oleohol. m natu- othoxido am... no added mom: on. droppm; m1 a: h 3% no on!“ on! Itimd tor tittoon oimtoo “noun: tho Edition of Iodin- othooido oolution. Tho nit-05m no oontinmoiy pooood into tho oolution throughout tho nation. Tho otirrod oolution on hootod to ito "no: toga-om Ind 151.5 g (0.23 onlo) o: othwz ammummmmmmmuumu pooipitotioo 0! India which. Follo'oing tho oddition o! tho°< wholo “.mwnonfluldtormnd ooolfbouro,ondtiltmd wootillhottoraonthooodimbmido. Onmlingthol'oootion m, 1.5 g or /,,6 Idiwhthyl dinltido prooipitotod ond mu on Md by tiltrotion. Tho tiltroto ooo «mutated to o 100 I1 wluo, dam on» it on moon-7 one. to mu tho nodu- bmido by 1:8 filtering to provont “59““ lumping. To tho arm-So product no than oddod 60 ll of voter to diowln tho loot of tho oolt; tolloloo by oxtroction with 203 ol 0: bomono to own tho promot. Tho honoono oxtroct woo “shod with too JO :1 portion of voter, one! dried «or onlvdmuo oodiuo onlroto. Tho dry bomono oohtioo no thou roi'luood with Korito too tiftoon W, filtorod ond tho homo” ooo mus-3 on tho otou both. “to: moo}. of tho oolnnt, tho yolloo liquid no diotillod in moo to yiold to g (0.15 001., m) at o oloor ”110mm oil boiling ot 150-151°/0.S I (oil bath tomporoturo 220-230°C). Ito ptvoiool oonotonto voro oo fallout 3:5 1.59913 (125 1.1.3013. W013 of tho coupound :or oultido num- (29) am tho following mum Colon. £01- outlaw... 3, 12.13. Found: 8, 12.155; 12.28. Betta-1 J-thiophonarl pmpionoto Qo-cnmfiogm Tho mm. 7.2; g (0.00 oolo) or mm ooryloto too am drap- iiootohhcmjyooolo) orchillod tbiophonoloootoiningom got nopondod oodiuo oothoxido oo o ontolyot. Tho roootion no oars-too out in on opporotuo count-ting or o thou nookod nun tittod with o storm, dropping rumol and ”no: condemn Imam capleto oddition of tho oothyl ooryloto, tho roootion nixtm no otirrod for o period of oixtoon how-o ot moo tnporotwo, and than filtered to omen tho booio ootolyot, out o hill mount of polynoriooo «tor. Tho aux-noted m ootor no mud madov reduced pros-sure an: the rooidno no manna to ma 7: g (0.37 nolo, 92%) or the no.» boiling at Leo-153°112 m. Tho format- index of tho amount! ml 11:0 1.5510. It. ”potter: (:6) mum oenotmto m. b.p. 153.19%) m pf," 1.5m. 24 ,6 *hiotldenyD-l-pmpoml cu. HCR an I! ll ’ Moth-oonookodutor a»: mud “mom, announ- «mummzmpmdaasnmahumnoun-um. oolnuon of mu:- oludm- Wide. mmthgCogs mo) of m1o4flmm1)mptmumm1mu1mdum Mammauumumumnntummum mmmoofldm.hmmotm1oumm to Ina-Io iho "lotion man out" bo‘hto control thorium roam. Ana-tho «mum ottho “.mnmuflmmmr omwmummmommmndenmdbymomg thoulnuontnonmbtthondommuolyoédiufinl o! othyl now. u om. point on. lulu. boom vary flmno and on additional quantity amnotmmmu. mumm-ormmxmmm hum-lotuonm,ond7molot1mWouidnooddodta 50 boo-woo tho moploo olooholoto. Tho othor 1am:- Ioo oopoutod om! tho ow portion on oxtroctod Moo with 150 I). mutioo of othor. Tho “blood othor loom-o voro cooked with 10:) ll of 10% Indian bio omuoto mutton, thou this 100 ll of rotor one! and our mm anam- Inlhto. mar ran-ova a: up othor, up mud ooo «mum woo mum to obtoin 22.3 C (0.13 ooh, 81.57%) of on moot color-1o" on. boiling ot 120-123°/1 a. Tho physical oonotmto of tho mourn! our" 3:5 1.580;) d6 1.2073. mm. of tho compound for ninth “Hut (2?) [on tho following rooultu Colo'd. for camsps a, 18.39. roman: 18.152; 18.90. 5 mad pupa-one: or the m: eon-tad out oo dumbed ohm, "to o yiold which woo o 11th better than tho {trot coon, 67.5 pol-amt of tho timrotiool, and tho product bound ot lbO°/S no; on llama“ procoduro woo doc mood to prop!" tho om compoum. hto o 100 I11 nook tittod nth o reflux oondenoor ooro ploaod 29 z (0.25 ooh) o: Mhiaplmthiol, 17.1; x (0.3:) m1.) at Moldy diotfllod um oloohol ond 0.25 x 0: mm. The own" no hootod undo: nth: ta tmtyntanr ham. Tho roocuon nixturo woo diooolvod in 50 m1 of «hot and mind tint with throo L0 to]. portiono of o 53 oolutian or Indian men-om... than oath oao L0 :31 portion of water, follow by dry- in; our onhydrou ”granola sulfate. Emu}. of tho other and «mun.- uon at tho mam yioldod 11.6 g (a: .06? mla, 25.6%) at tho meiy “Hilda boiling at 120-12350. m. The campeumfi had tho following phyoia «1. amount” lags 138523 $25 1.2375. Analyoio of the cwmund for Celtic’s with: (29) Provideé tho following results: :3 Colc'd. for afiuzzw 5, 3.3.3.3. Ewan U51» 17.94. A moons: proprotion or thin Wow mo carried out in o nit-roam om'oopLoro m: rooultod in o 33;; non of tho desired :2th omen ' diotillod at 123-1237" m. 24 ’5 mama-1) ~l-mtano1 ca. ca. 8 Going the owe oppoz‘otuo so no doom-food obovo, 50-0 on]. (0.50 halo) or oononolor lithim allusion Wide oolotionvooploooo in tho nook and trootod an: 108 a (0.1.7 nah a: um M flnthiothionyl) pmpionsto at ouch o rote oo to oointoin gentle venom: at tho otheo. rho reaction mixture ooo otirrod for fortycfivo aimtoo, mind, our! ottvl ooototo mtioooly oddod to dootroy tho one" Ivorian, ottor onion tho Iixturo no pound into 250 .1 of ioo rotor. The oooplox oloolmloto woo own- poood with 1509 ll of o ton pornont solution of oulhrto ooid and tho other loan:- no ooporotod. tho ow hau- no oxtrootod with time 125 :1 portion or othor. Tho cabinod other Won taro driod on: tho othor mm. oubmmo diotinotion at tho product 31916.04 7:. 2 (3.1.0 mu. 61.2) or o 11.3,: 7.11m oil which boiled u.- m~m°/o.s m (on. no: tauporoturo 155-176°o) . Tho piqued proportioo at tho murmur omido mo dotominodl a? 1.571;?) €125 1.1710. Anolyoio of tho oun- pound for oulfldo mimi- (29) mo tho tanning noultu mum. to: can“): 8, 11.01. human 3, 17.149; 17.150. 2-( ,6 ~thiothiew1)-1-pontonol ma, ca. ca, U341! {SH 301'! 3 The oomo gen-rs}. prom-km so pmviously dooori‘oofl was 65%;3103‘051. tiling £10?) :1 (£3.50 owl-o) of o lithium olminun tmiddo solution mm 130 3 (0.53 hole) or ethyl 24,6 athiothionyl) Valoroto dissolved in 159 :1 of oxfizy'drouo omor. Tho omooo maria-2o and oomph: alootzoloto woo docummood in tho mo]. humor. moo- tho other oxtrootion of tho hydroxy ouli‘izie, tho other lover-o oar-o coalitions! , whoa with wdim bicor-bonoto ond water, dried, ond tho other moo-ad. Froctionotion of tho crude product goon 5?. g (3.1315 solo, 8229') of tho pm Map-onus! Ihioh ammo-.1 ot 133-13500/05 no (oil both twperaturo lea-159%). Ito physical proportioo moo as; 1.55.323 d25 1.13%. 'tho oulfioo Moo- (2?) onolyoio of tho product gavo tho rolloling molt” emu. x...- c.n..s.m a, 15.53. roman 16.02; 16.15. Zwmxy—l-pmponol on, 0.04; 33.1»; ,3}; Boinz tho mo toolmiono oo thot w in tho foregoing Wu. 60 g (0.31 ooh) of ethyl oLophomzq propionoto on added to 310 I1 53 (0.31 male) or s cache male .91an 0: 1111.121: almimn Madrid-e. The reaction antes-u was stirred for as am hem- poried and the ma. wands was dewmmaeax with ethyl acetate . After filming tbs um- te Item overnight, the complex docimlato m decnmmefl by pouring it into 300 I11 0! to. water and “flag 1290 1:1 0! a ten percent sulfur“ aid Deletion. The ether laym- m “pasted an! the «men: by“ “trusted with two. 158 I11 pea-tie” e! am. The combined other layer- were Mm! With 200 I10: I {in pomnt Judith bicarbomta solution me then dried. fitter moving the other, the product was dil‘bmfli to ovum 10.5 g (52.27 mle, 56.5133} 0: the pix-9mm" menu boiling u. 1259/10 In (an bath tnpmtm 160-165°c). It. physical Mutant. at tho mane m3 1135 1.5239; 625 1.3232. The reporter: (15) alum m: am. 12091:: m 11:5 1.11154», «:25 0.913;). I. weasel preparatien cf the compenmi on a mall ”do (0.05 3910) malted m a 6 a yield (7‘33 0! the timer-cued) of tho phemw alcohol manning the {dilating physical cantata: tap. 122-l25°/l£> u; 3?; 1.5232; a” 1.0532. In ancier to test 0 second general wthe.’ 01' 831115118811 , 11.3 c (6.143. I010) of Iodlm ma 130 ll of 0513-15de 13:: wepyl other Ian platen} in the apparatus previously described and a solution or 22 g (G . 3 melt) of phenol dissolved in anhydrous hoprepyl other In aided llmtly. The flak I» named slightly to initiate the reaction. After the media had reacted, 29 c (0.21 min) a! zéoMom-l-propml we: added ms! the 3mm m reflux-d rm- m eight hour pet-toe. It use than trmfmcd to a «putter? m1, washes? with 1% m1 of water, nut um two 50 :1 pox-1.10m of o t1” percent 302.1112: 113mm. relation om again no: rotor. titer tho other ”lotion bod been dried our mhydrooo m Iultoto, the other no two“ one the far-orient mm to yield 19 a or o aster-1d. boiling at 60-63710 on. Tim planed propertioo of the liquid mo! 11:5 1.52533 d2; 1.1309. The notoriol Mdontly W . puns-11y of mooted phone). no moral oitroottooo with o ”lotion or oodim Ivor-oxide motly "(hood lto lolmo. 24111019231314me ml on, Game .011 Follow; tho out: pronoun so in tho pronoun proporotteno, 9S :1 (U .095 mole) of o ono solu- oolution or 11mm am woo woo ploood in tho flak, coolod and trotted may with 23 g (0.095 Iolo) of W1 24mphonyl mpiomto . knowing tho “nation of tho «to:- , tho oootootoottbo nakoero out-rod for opouodoronow ood o W. Auoloolmoototzvlooototouo doodtodoommothomo worm- ond odditiaool othor no mood to imroooo tho fluidity of tho W oixturo. Tho complex olooholoto no (Swampland by wing 200 ll of tooootorondwonototonporoent oulhu-io ootdoolntton. Tho product In unrated, washed and dried in tho moi room. Bml of tho other Ind mum» of tho mlduol liquid yielded o forum or 3 g and 11.5 o (0.07 solo, 72%) at tho ammo compound boiling at ‘1." ’41 111.1187 1 m. The refractive mm: or the :1th m: a? 1.5722. Tho reported (12) pmportioo or thio empeund oral b.p. 9£-100’/0.5 -3 1150 1.5710. 24 ,5 duemphthyl) ol-progzxoml ca, . (Bandage follofling tho om gomrol procedure fiocuoud about, 25 g (:3 .10 solo) of otrwl 24 (doudanqahtlw’l) proptoneto diuolud 1n 50 ll of onhydrooo other no mica-w mm” to 125 :1 (o .13 m1.) at 11th am hydrido oolntlm. n» mitten woo nth-rod for ono bolt hour ottor Mob othyl mtoto no oddod to demon tho mmhymeo. Tho mom "notion 1:an no pound into 100 ll of too rotor and deoompoood filth 600 ml of o ton pmmt oulfm'io ooid ”lotion. that product no extrootod with other, mixed, Ind dried on Moro. Tho othor no mend by distillation and tho rooidud on ooltdin'od moo ooolod nmmbtth. Thooeapoondnoltod otmutuporohn'omamdlo- ttllod in new to yield 18 g (0.05 ooh, 83%) of o pol-o mound mob boiled .1 160-1! “70.5 on. Tho «tram. 1mm at tho new no. off 1.6%. m 11:11:11 «114111.: to o mm and upon mm; and u. uoltlng pom deter-1mm mp. 26-28%. Andy-1o m oulfldo mm- (29) of tho product (on tho tanning rooultou emu. ter cuxwm a, 111.67. Faun-fin 121.92; 111.99. \J't cu in atmpt was Harris to prepare the cerzpmm-L? by refluxing I mixture of {5 -tbionq>hthol and .1131 aloohol in the presenco of 8111111? for twenty-four hem-o but rmltod only in tho reoomry of oomo / ,g «1.1- mm 13161 mace and more acted Athiflnughthol . 3"‘hiaphom’1~l-rm p one}. ©443.~:Hrca,am By o oinilr maxim-o involving tho intonetim of l2? :1 (a .127 m1.) at lithiu- nm hydrido oolotien one: 25 g (0.127 oolo) or mum (J-thiephoxvl) prepionoto dioxin: in 103 ll of obooluto other tollmd by doempouition of flu omooo tum-ido vith othyl loot-to than no obtoinoé o viooooo ”lotion or tho mylox olooholoto. Doomwoition o! tho oeoplox m oooooplimd oo dooorihod pnvienoly and tho othor oxtroot of tho compound on washed one tried. Artu- roaming tho other, u:- 1:th on 41-1111“! to yiold 17.3 o (0.10 Iolo, 181) of o um oil boiling ot DHBS°Il ll. Ito ntrootivo indox root of 1.5807. Tho report“ (31) physical mtmto for thin compound on: hp. 1311.135? 2 a; 1.11230 1.5813. WW' ’ 1-( ll Mondewl) #11113me 341,-czz-czx, U D on: Into 1 three neckei {la-.3}: fate-.2 with a a'thzr, reflux can-1mm: mi dropping formal, were placed 11%.}; g 0.1.? 34015-1) of 3~fi1iqwmrwthlol and 121‘ ml of o tmt: gnu-cent solution of Ito-15.1121 Xvi-next fie . 1. quantity, £531.93 3 (53‘ .318 male) , or premier»; chlamhgcbin wan oxide-.1 drowns over o moo-half hour period. The romtiam miztom was mflmi for o patio! of one hour and We! to owl to roam thgoeaturo curing which the o yellow oil ”mated. The 01):; layer was aspen-out Ind. tho moon: log—1r oxtrootod with too 59 I]. portiono of otlmr. The other extract- oore oun- bimd with tho oily loyor, wash-M mine with 50 m1 portieno of water, and dried ovor 11:1de oodiun mat... me:- maoung the sum, the mum on diotillod un-ior rezone“ pwlflm and gave 5?.5 g («‘3 .311 nelo, 5.535) 01‘ 61.3: yellmlllh Gil boiling; It 1160/; am. Ito 33313111303. Gem- otmto Vol-M this 1.57533 425 13.111. The reported boiling point is: 115°]; m. indyfoio of tho compemai for lulrine 3111111? (2'?) gavo tho following data: Colo'd. for 073,499.01 8, 193.110. Foam: 3J1?) 18.110. 1-( ‘6 ~t}:;1otlziorg'l)~2~butm1 M 533* H’Cga‘cg 3 OH 8 Using tho om opporotoo u no melon: in tho previous preparation, 31 g (0.18 .010) of J-thiephomthiol mo dist-elm in 50 ml of abooluto othonol and trotted Iith 190 Ill of o solution pmpored by oiling 11.2 a (0 .18 solo) of oosfiuo to 1-33 :1 of woolen oleolml. The rotating 58 caution u- then mod and 20 g (0.12 ml.) or butylm «mam add“! dram» lulu tux-ring. The tmparatm of th- naouon mixture no than mind to it. reflux ‘mutnn and name! gently for an hour Mum. mummsnmumummmt, the 50¢.sz am in. mm to "new India 0W0 mun I'll nun-mu: Mod and ”13:19:! to at“ 9.5 g of “1t (90! of flu theo- nma). m mum. m then mutated, «31an in my, mummsoupomoaaanwpmm‘mmumm warm undue Saulqnanuunotnm. mouth” ham-m dried mruavdrmudiuwnto mmormadngmmw-pmmmt u- «wanna a yield 15 g (0.09 male, 53%) o: u light you“ liquid mum; n 116-118°/0.S an (on m Watm‘c lac-190%) . m phylit all eon-tans warn a? 1.5755; 1125 1.1751. mm. m (29) maim- ot tho Impound gnu flu touching “lulu: Cale'd. for mango: 8, 17.02. Poms: 3, 17.31, 17.29. 1-( p .miommi) ~2-yontmol WW ‘ frfifCHfiH-E; £33 3 The pmuduro and apps-am for the reaction was the sun In that m3. in tho preceding prep-mutton. A quarauisy, 26.6 g (0.23 .010) of Mdnpmuucl m din-01nd in 50 :1 of Mute alcohol, placed in “an that uni mm rand); with I solution at ”dim 0mm mm“ by diuoltlnsg S .3 s (0.2) m1.) at mam in 1m til of absolute aloohal. 59 Th. Hanan Man m but“ and stirred far a parted a! twenty wince. row by mm.» with 32 c (0.25 ml.) at mum-2- Wm]. which an added em I m aim“ period. The nation m III mm n it. an“: twpan’mn for a period a! can hear, «clad, tutor-0d and tho doom moved by dutmauon which run a 4m «loud man. no and. prodmt no dutch“ in on)", wind, «31-1021, and arur mung “A. Other, tho euapoumfi in distilled $0 m 33 g (0.16 ml: , 715) of a numb on which mum It 12$~1ZI°/b.5 n. The ran-mun index and density at the acmpound mu 3:5 1.5636, 425 1.1397. analysis a: the mum tar nix-‘15:: WW (:9) gm the «new; result" Calz'd. to: Cfiuflafix 3 ‘ 3.83. Founfin 3, 16.1?) 15.11. 1~( fl ~thisupi$lgl3 ~2~pmpwo1 ~5-carczchzz, Eli The an; manta. u patiently described an an: and pro‘rinion m m to bubbh I It“. 01 dry nimgtn g'u mgr; flu ”notion W. a quantity, 1.6; (0.16 mu) o: (ngfllfil m mum in .muamuamxmnmlsouo: mm alcohol. throw us hubblod Mg}: um syntax and continued thmuzhout the function. Tbs Wm wan kept. 03. 60-79% am? W until tho (8 41x10- whthol had omplnhly mmlwd. It «Dilution of with: “karma was prepared by dumlflhz 2.} K (0.10 mob) of ”film in 1% 21 a! (malaise “1161301 tad “an: to this ”Mum flask. ”tar Itirring than hat ”1:;th 61‘) for a 1.5.1! hour period, 11.1: g (3.12 310318) or pz‘ogaglane cum-0223:1391!) m ufided quickly am the arm” was mflmfi for n pen-10d of an hour and a half. The hat-t solution was filter-3.3 to 3’161'3 5.5 g at mam cliloride (PM or the tincreucal) and umn cauling tho filtrste, 1 g or K , (6- dL'xaphtfiyldlz'alfiaia crystallize-.1 {ma thus reaction mixture in the for: of divas-y plates (33.12. 139—129”). The (“1831111416 was remixed by filtra- ugn tollowd by removal a: mat of thy 31¢».ch by distillation. Upcm coding, the prod-.1“ crystallized, vac-u filtered our! driad. It mum: at hl-LJOG . After crystallization from a 53-530 Mum of own/1 alcohol and vat-er than was chub-zed 19 g; (3.6-? role, 57%;) of light 3.11” mm melting at 1.2.1.295. Analyst: of tin remand]. rm- lulfma sulfur (29) gm the following results: Calc'd. for Cufiuffil S, lb.€.7. hum: 8, 153.13) 1".10. 1-phamxyv-2-pmpam1 .0-323 342-3412;, (51'! i quantity, L32 3 (0.16 3019) , of pheml nu dissolve-:1 in 152:) n]. a! t tan parcent 30:;le ls;«.3rox1-..Ea solution we“. interacted with slightly man than the uxeomucal want (LE 3, 0.1.7 male) or propylano calommdrm. Tho reaction meets-adad rapidly mafia:- reflux filth tho ”panting: at In oily layer mi was complc-M in a hilt hour. The oily layer of tn. prodmt a: «mum and um thoul layu- 0:6:er with other. ma other oats-acts and oily 19;?” var. manned, washed with a {in percent ”dim hriroxioo ”lotion, follows! by motor, dried mi the other mono. tantalum at tho product gm :8 x (6.25 non. 55.52:) a o colorlm on boiling u no—ufno n, m physical oouunto m. n13? 1.5220, (125 1.05%. 1.1%.er (15) "loos for its phyuiool non-mu m: mp. momma a, n35 1.5230, a” 1.0510,. A mood propoution of tho compouno resulted in o fii gram of a color-1a: liquid. boning o: 113°fl no. In "truth- index van 3:5 1.5220. ' zommobl-prooml @o-czzrcafizzrm Following the previous amoral proooi'km, 21 g (0.22 :01.) of phenol m diuolno 1:: 90 ll of I too pmont solution of mix. hydroxide and treated with 22.5 x (8.22; solo) of Mqhm' ohlorohydrin. Thu um:- tm as "(loud for an hour during which an on; layer “proud, mu m mono ma tho mm- 1-5;” extracted «uh cum. Am: combining the 011: 113m- Ind other extracts, they are who-:1, driod, and us. other removed. Yawn diotfllotion or the product 31ch 29 g (0.13 solo, (20%) ot a oolorluo liquid boiling a woof/lo ID. I“ run-nun Luce: rm “gs 1.52M“ Tho reported (32) boning point for thin cou- poond 10: 2149-2507751; an. 1-( fl «biothionyfl ~2-chlor0propm s-cn,-ca-cs, t! a Cl 8 Into a 300 31 three memo that fitted with n m, reflux Goodman and dropping fmmol an placed 25 E (0.11: .010) 0! 14/5 «thia- mWIM-propmz dissolved in 15 m1 at pyridim. To thio column can mm with tuning 20.6 g (0.11 mic) or purified mum chlorido dur- ingtnbour. hammnvullaouodotopmodwltrouotdryur mu the tort». of tho Iixtm owing tho reaction. Stirring m continua! tar fifteen limit“ m the mention of thiml Moi II: caplet-0. The reaction mixtur- m the: tan up in 80.11 or othcr, III-bod trio: with to :1 portion- of rotor and arms our moron: Iodiu “lint... Following the moral of tho other, the product no diltillod in room to 3191:! 1o 3 (9.05 min. 31:) or ”mam oil boiling a. 85-900/1 n. the Mod mutant: of the «impound were: of? 1.57914] 425 1.22m. Am 1*» «1m. colmr (29) gap the taxman; remit” Galo‘d. for Cfiififill 5, 15.62. Emmi: 3,, 16.614; 17.03. The oonpcma no the pupa-M by tho romangomnt "notion using on chloroform u the reboot. A quantity rm 3 (0.10 nolo) o: 2-06 - thicthinvD-l-propml as (involved in 25 :1 of dry cum-arm and mum um: 11..) g (-0.1: m1.) of purified mom chloride Mud in 15 ll of chloroform The mixture was than renamed gently for In hour during which tho Velma of chloroform was kept constant by «animal notation of oolmt. The chlorofor- no than mod and tho product diooolvod in our", “shod with Voter, cried and tho oolvont ogoin mono. Distillation of tho pmduot govo 13 g (0.07 nolo, (Sui-:15”) or on dnoot oolorlooo 11mm boiling a min In. Ito rofrootivo indox out of? 1.5800. inolyoio of tho ohloroooltido for «mm mm (29) gm tho follouing dotot Colo'd. for 6,393,513 8, 16.62. Found: 8, 16.523 16.66. A mono proporotion Ming tho om contusion of uteri-lo 3m o 55% yum at tho "W chlorololndo boiling u 115-11773 on. m rofrootivo index om n35 1.5793. A third proporotion of tho oonpmmd in which dry pyridiao m mphyod on tho Iolvont govo o 26% yield of tho ”manger: cum-«mm. boiling ot wow/0.5 m. Ito rotrootivo no.” not a? 1.5800. 1-( ,3 othiothiwlfifl-ohlorobutm mo! 2-( ,6 melfil-ohlorobom cu, ca. EOE.“ ago—c3423, l l c1 I 8 ‘8 Tho prooozinro and oppflotuo on tho om a pontoon] doooribod and com-too or dissolving 1o 3 (0.053 ooh) a: 1-( ,6 wk:- mtonol in 25 II. 01‘ dry carbon totroohlorido followed by troohont with 7.1 g (0.306 mlo) of poritiod thiooyl ohlorido diooolved in 5 ml of r3:- cox-boo tctrocmorido. At tho end of the oéiditioza, the mixture was ro- tluod gcntly on tho otoon both for o forty-tin minute period. Mtor diooolving tho reaction omuro in other, it no homo with three 20 I1 montitioo of rotor, (trio-d and tho oolvont moved. Tho pro-Snot no Woo undor vacuu- tc yiold ll 3 (0.05 sole, 5%) of o light yollmdoh oil boning a 92.91”: .5 an (oil bath tapcromro ITS-195°C) . rho phyoicol coast-nu of tho oixturo of 1mm our" 11:5 1.57113 dz)5 1.2035. Tho “11'1“ oulrur onolyoio am the {alluding Poul“. Colc'd. for cans-Cl: 3, 15.50. Found: 3, 15.703 15.137. Tho mixturo no an prepared by tho roomrmgmont c! 24 fictitio- thionyD-l-butoxnl by trooting 113.8 g (0.10 ooh) at tho moron ammo diooolvod in to no. or dry carbon totroohlorido with 1b.: 3 (0.12 mole) of purified thionyl chlorido diooolvod in 10 Ill of corbon totroohhrido. Tho mo]. operation were carried out ood cictillotioo of tho promot yield“ 13 g (0.06 nolo, 63:5) 01‘ o mixturo of too "Wing“ and moroc- mmgod chlcrcoulridoo boning at ion-13290.5 m. Tho roiroctivo 1mm: Ind dormity moi n35 1.5712: 625 1.3 7.78. Analytic of tho mixture for oulfldo mm- (29) gm tho ramming roam-a Colc'd. tor wusgm 5, 13.50. rm: 5, 15.95; 15.77. A name! proporotion of tho companion by tho romongmont reaction rooultod in o 65.531 yield at tho chlorooulfidoo boiling ot 96-1o3°/o,5 In. Tho rotrootiro two: out His 1.57137. l—( ,6 MetEdsm'l)-2¢}&omw 3158310 and 24 (6 damn-Aorta) «1-6 man-ope utm- ca, ca. cat. ,.is.-ca«cfi.-ca.-ca, mag-1 I I I] C). I! ll 3 .5 Wing tbs In: gypsum mi moi-mum u duct-159d than, 16 3 (0.08. holds) 01" 14 (6%}dofidaw1)02-pentml mo clinched in I) ll of dry carbon wbmmsmdn and ranch-d um. 7.6 g (0.01 .91.) a: purifiod Many]. fluoride diuolnd in 5 a}. of carbon tatrmhlorido. Identical quantum we're carried out a Newly described and {gamma yielded 10 3 (3.03 non, m) o! a. mixture at «nun-0mm was: hailed at 110-11275 .5 In (oil bath temperatm 175~1953°C) . The physiod cou- um!» um: a? 1.5m, a” 1.15;). 1311mm“ or m mixture for cul- flda Iulfur is indicated halos. Calc’d. tar 6,833.61: 3, 1h.” . Fanatic. 3, 11:33:11.3)1. ‘Eho [imputation m the emit! out. by the pmd rawrmgmmt of 2-4/6 othiothicnjl)-l-puntaml. A quantity, 1152 g (0.12 ml»), of purified fiziorgi‘l ohloricia was diamlwd in 10 51 of carbon tetrachlari‘io and Iii-dead (troy-413a to 20.2 g (0.1-0 male) or me wax-ow Bulfléa Muelwsd in LO :3. of dry cubon tetrnhloriae. 11m product. was ilDII'tai‘i by carry- in; out the previounly distant.” ozwraiionl and retaltod in the: prop!!!- tion of If: g (0.07 3010, 7355) 61‘ the mixture (at 1m" balling ct 122-1Zh°/0.5 m (011 btt‘u tmpm’amm 173-13565) . Th0 following phyliall proportion rem detazninecin 11,33 1.53133; :33 1.5”?13. l- c‘ulfida sulfur {:15 «111141131: gr.“ the tallwing ranks: (inlaid. for 093,133,171! 3, 111.530. Fauna! 3, 11.353 111.87.. A ween-:3 rm. third mm: mm mm inmlving the partial warrmga- mint of 2-( (6 ~t11iatidewl)o1-pzmttml with “1101\3’1 chlorizis and ran-- tultaa-i in 311211133- 0! 63.51 and 1.111.392 reapectiwsly c! 11:13 ehlarmulriéel The bailing paints and rafraetin 111121113120 were respectiveiw 112-1189] 13.5 um; 11:]. 5101 111111 115-122 /:).S m: 11525 1 5:113. 1-ptmmzq-2-chlar0propam @44113-8 21-131,I 1'01le the ganaral proeefiuro 111301.13st men £111- £113 convarsion of M13033; aulfir‘ian to ciaorooulfidm, 23 g (3.15 mile) a! 1-1111.me pragaml warn (115301 11-5-11! in LI} 311 of dry pyridine 0.2.111 truism: newly with 23 g (0.17 ml: of purifier. thisnyl ehlarizs . Tb: ”mum: mixture bo- cme m from the cmthamio reaction and tho pmipitdion of pyridine igcirachlorifie km: 1110 mticaabla after about. half of the thionyl (ables-i159 hr: bean added. Tho mixture m “1an «11 “mod far t half Mar :11nt tha iridium at unionyi chloride. It. in then taken up in other, “531121.! with water, dried‘ and the film moved by distillation. The proz'iuct on 11111111111101: boiled. at. 9S°IS m yielding 111 g (0.03 min, 5532!) at the dash-er} corpound It: p31 sic-J. constant.- wrs u renown 11:5 1.5252; 1325 11.11.39. 1111119111 at um coupon-<1 for carbon 1m 313113013311 gave tho renewing results! 67 Cdc'd. tar cgumn c, 123.31.; a, 11.15. 21:11:11: 1:, 611.1211: 8. 13.813. Author promotion at tho Ciao 0-:an gm I 357% yield or :1th boiling It 9575 H. Ito "frostivo 1min not n35 1.5221. Two ottmpto mo auto to pmporo tho chlorido by a unila- r91- oction in which tho pyridino solvent m upload by chloroform mud in ouch trauma tho product obtain-r! gavo o negative toot for chloride ion in tho oodim fusion toot and no ovi-fiantly mooted plum pro-pawl. lfiiaaro-Z-fimmv pmpom 1:11, -c1-ca-cz1.c1 UMW (35-1) “um-n11. mmmmm Mm ond opporotuo and in tho wounding propoutioa, 12 3 (0.06 filo) of 2-9me m trootod Ilth n z (0.10 uh) o! puritiod thionyl chloride. in in both woo nod to moroto tho outbox-lie nationwiohvuotimdtoromtmtonofiutbo thionfi ohlarido oddition. Attor gently booting for on how, tho thick rotation war. no pound into 513 I]. of rotor to canola tho pyridino hydration-Mo. lwnmutyotofim'moddodmd Qua-utmtronoromdtoo ”watery man-1, and tho voter 1w rum-w. tho lottor woo oxtrootod tit-how". Moths-layman mm,mhoduththroeh0o1 partial“ of o diluto caution of harrimmnric acid, twin vith voter, Mod-adthoothorw. mommtooodiotined inmmto giro 7 103.911 um, 521m 1 11111-1... oil mum; u war/11.5 an. 111. photon. can-ton“ or tho compoml are. 11:5 1.51.953 113° 1.5216; 625 1.0921. 1‘11. reported voluoo trot Lp. 110-113°/22 u; 3:0 1.52183 11'0 1.102. A carbon one! 11-,qu molyoio at tho W govo tho following result” cac'd. tor cguccn c, 53.31;; H, 6.115. Found: C, 63.1.32; .11, 6.82. 1-( ,6 othiungnhthyl) ~2me Gama-w- Into .2063-1 Erlouoyor Mompluod 15-10: dryohlnrotom containing 1; a (0.018 I919) of 14,6 -t1:ionqaht1wfl«2‘pr0pm1 oar: trootod mm. 111111: 1.5 t (0.1m mic) or puritiod thiorvl «111112-1119. Tho flak no ohokon cont-11m]; during tho odditm of thicwl emu-16o. Is our otrau or dry o1: no airoctod moo tho ouri‘oco of tho rotation mixturo ot {tomcat intarnlo throughout tho nation, to i’ooilitoto ro- und 0! Guitar dioxide and hydrogen chlorido. Tho "action Mm tmmmmnrmiumodmmmumtaromm poriodtoomplototbomnlo! can. Thonixturonothonmwlvod in 50 I]. of other, nomad vith firm 20 m1 portion of rater, dried, tho othor mood mi tho promt diotillod nnéor mama to yield 3.3 5 (0.01): min, 80%) o: a 11m yellow liquid boiling at 11070.5 11:. Ito raft-nth. 111611: and dammit: mt a? 1.613653 4’5 1.1711. Amino. £19 «wwmmmmmu-(n) mmrmgnmm emu. tor casual. s, ”.52. rm: 8, 13.96; 13.911. thou-o oupmndm dupe-pm ”mama-moth ( pwtmud-pmm wing o amino proudm oo no .910)“ in the Mon-1y donut“ noctiom 1 my, 1 g (0.03! I010) If tho Mudfidomdiooolvod in 85:11 «dryohlmtbn Ind trootod um 11.: g (0.036 on.) or win-11 thionyl ohlcriéo. the :1:- tmmmodoothoommforflwmuoaflmthon- lotion one to drivo or: rooouoo goooo. It too the. fliooolvod in othor, now: with m. Mod, nan-11 m- o Mount-o um. Ira-no, mm, ma tho othor wood by “motion. flu route”). ”out mpwwoOJmmtormhow-(oflhhootmuom m)umuoimmumyimammm. m W11. mam 6 ; (0.025 Iolo, 79:) and no mun ind-x om €51,636». mutton-19m mmruiuiurmiu M “limo lulm (29h Colo'd. m 01.333111. 3. 13.52. Found: 3, 13.901 13.75. 11 30-3 :1 three mkod flak m fitted with o roam: condom», lunar, m1! dropping m1. 1- qumtity, 10 1 (0.115 min), of mm: Ioro plat-11 in the nook and trootod with 112 g (0.115 ooh) at phonol Mood in menu W1 other. no hour-om Iixtwo III 70 renamed until oi]. the oodiun boil oiooolvod ond 66 g (0.115 mole) of ol-mpropmm .1114 clinch-ad in 50 ml of ozmydrouo impropyl other III we}, otter which tho mitt-m no refluxed for oight houro. A ”lotion of 2 I]. or «Montrotod hydrochloric acid in 203 a]. rotor no oddod, tho nixturo ohms, ond tho other lmr ooporotod. Tho mono loyor no extract“! with otiwt. Tho combinod othor oxtrooto Ioro driscj, ad the other mend by diotillotion. Tho running uteriol woo truncated ond tho mooted phoaol callootod at 5545"]! n lowing o rooietuo in tho aiotillotion nook ohioh cry-tolliood upon mung. Th1- lotoriol loo mum: in other, hoot-d with liorito, tutor“, on! tho othor mood. Rooryotoniutioo of tho oompouud tron urban totro- chlorido yiolded 3 3 (0.92 ooh, 111) of tho puro mid. Ito Iolting point not 116.41%. m- reverted film (33) m 115-11612. 2-1: tiered-Prepaid era-721ml, 01-1 61 Into o (mo liter throo necko-i nook, inorood in on ico both, owl placed a solution of 135 g (1.0? solo) at curacy]. chloride customer! in 300 o). of cotton tetrachloride. Tho {look woo fitted. with o otirrar, roan: condom and o pious of Elmo tubing which oxtondm helm: tho Mm of tho Donation. Into this rapidly otirrod c0113 solution, propylono m bubblesi until the: color or the chi-owl chlorides diochergerd Ind the {look bl“, gained 29.11 g which ”Responded to 0.763 male of promrlono. The loud vac tutored, '15on m1! Twirclyood tit}: c013 71 ”6113 bioultito lolution. Tho ammo ulntioin m ”th with Iolt, mm with othor and tho oxtrovt Mod our anhydrouo ”dim “Unto. Renown]. of tho othor Ind dmmotion ot omoophoric promo gm 26 1 (has) or m ohlmtwririn mm; a 131-132°c. Ito Patna- “to “do: In! éS 1.34358. Tho 3,5-dinit1-obommo at tho vapour! ”1m at: 73‘75‘5. The W reported promtioo 93‘ this am- pound om b4». m—uu’c/eu an; :1? 1.14m: mp. at m 3,54!th- bmmo. 76.s~71.$°c. ' 1-Chlm-2-But anal mama“ m 1 may, mo 3 (0.80 ooh), at dimtmrl chlorooootol out! 72 g (0.8% mole} of mm oxalic acid vet-o pimd in o 500 :1 mad bottom float tittod with o 12 inch ”gram: aolum arr-Mod to! Wotan. flu flux us come! mplotoly with o honing until om! o Iototy glou no plum”, in front of tho woman no I vocation ogoinot waldo "plantain. Tho notation nixtm-o m hootod womanly mourn; tho .1" acumen of o mum». boiling in the rouge wafl’c. The mun». no xii-mind in 190 ml of mam» oim, plane} in o ono liter bottlo containing 63 g or panama oolcim china-ma 51mm. rho bottlo no cuppa-id vith I cork hum; o Moll hole to "110” pmonro ma choker: for than and 1 half homo in o mechanic“ maker. The hotel-om mint-o m mum and t1» who“ mama! to drop into o ohillod Manama nagmt pwpmd has 87.2 t ($.80 mile) a: radiotmcd mm 72 music m1 2.: g (0.53 ml.) or “menu. the addition Impound no dompoood in tho and humor with Soc 31 of o can to am hydrochloria laid oolution contouring m oauol Velma of crockod 13o. Tho “1:510 oolnuon In oxtroctod with tour, 150 :1 portion or other, which vow combined, Mad tint with 150 I1 at o dilato. mum-1e acid ooln- tion, timodthlSOolotuotar,mxtIith150nlototonpa-oont pot-ooh: ou‘bonoto oolution on! than: with .150 31 of rotor. The other oolution no driod our mus-m petunia oorhonoto tor too ham-o and than our max-on oodiu mm for oiaht WI. The othormiuovoémdthomdthinmtoyioldflg (0 .19 Iolo, 237:) at tho colorlooo alumna boiling a 50-55%; no. Ito Monti“ index too: a? 1M7. Tho toportod (3h) pbyoim omtonto mo hp. 52°fl5 II) a: 1.157%. 14m2~renm1 "O ‘V the momma and ”pantie me tho own as that describe-1:3 in tho woman; moratian. 1. quantity, 12L 3 (1.03 mole) of dimetiyl snow-o ooetol om: 90 g (1.00 male) or mnqdmuo oxalic «:13 were allows: to interact. in trwticm boning 1n the rum aim-95°C no cullected, dilutmf.‘ with 1&3 a). 01' obooluto om:- onsi shaken for o period at four hour: with powered “lain ail» ride dihyératsa . the roman; um; dram Wmtddewaa m mum: that}; into 3 will mica Maura 73 ”lotion ooziah bod beau waned by tho int-ration. in 559 ll of oboo- Into othor, or 25 g (1.10 ooloo) a: mm and 123 o (1.00 mlo) or "Wu-propylbmido. ThonixtmnodoocupooodvithSOO-l at o ono to ono hydrochloric ooid oolution containing crooked ice. Tho man alumna «- oxtroctad ma othor, mm: and mm to boron. Ito-cool of tho othor and diotillotion of tho product yiolaod 33 g (0.26 oolo, 2:35) or on. oolorlooo cum-own which tmod o Mdioh violot ooluo' ottor Ming oot ooido «ox-night. Tho boiling point of tho , ootoriol not M°llh u, out ito roportod "ht. (35) 1-. 59-62711. m. Ethyl eropionoto on, ca cog: h A quartiw, 198 x (1.20 ooh) o: °