Document 5DRb5GQqy77KJznwe4pdXXgo0

M arch 20, 1057 H alogen D erivatives of Die BNZo-p-dioxin 1439 tinned abnve -aa idded dropvwe (o i XO-ral.ether olulkm of pheoylltthtum, which hid beep made from 110 ( (0.70 inulc) of bromobenxese H u o c o i <4 lithium metal. After refluxing far ose boar, this react mixture u poured>onto cracked Ice dilute nitfnric acid to destroy the eices ihenyltithiom. The ether r u then removed by cvnporaloa, Im t d x a white solid, which w collected u>d dried. This solid waa plxtrrl hi a Sazhlrt extractar and ex tracted for ooe boor with 20-40* petroleum ether to dis dwriotlhystihsaotf ophcthneylbarommpolesUofanteh.e trim- obtained by the hy C.A5m0a.0i,; HC,al5e-d2,0f.or C*H/)S: C, 50-0; H, A M . Found: O r an ge of xyw-DiphwayMfafloTsoa by Bacxytm ire mi ma Chloride.-- A 23-g. (0.10 mole) taxnpfe of ija dipbenjddmkatanc in 25 mJ. of ether was added dropwhe to a 200ml. ether solution of benxyhnagpesium cb-larid*. which had solve the njetbyhrtphenyhilaoe (derived from the metbyl- been made from 03 g. (0-50 mole) of benzyl chloride and 13 phenylaaoe). The yield of this compound wax 7.0 g. g. (0-5 g. atom) of magnesium turnings. Tbs reaction (0.03 nsolc), m.p. 65-dfl'." The rematnbnr solid was ex tracted with tohseac for 13 hours to tire 33J) g. (0.10 mole) started Imtmediately and refl*uxing of the -soAlvent resulted.- ot tetrmpiraybSaae (derived from phenykOane), m.p. 233- ooe boor, then hydrolysed and worked up in the areal m a n 233*." ner. The ether was dktfllrd off and a 10-f. mixtme of Osovagw at xym-DfphawytdMama by Kthytmaggidam pbesyleOanc and toluene at 120*, tanvhg a rwddne Bromjda.-- A (0J0 mole) sample at rjm dipbenyldi- which waa distilled later. The mixture of pbeayfaflane and lilfmne ha SO m L at ether was added dropwisc to a 200-ml. tofaeae was treated with nbenyDHhimn, which had bare solution of ethyhnagrxsjaia bromide, which had been made made from 04 g. (0JO mole) of brosnotwnrrae and an ra from 70 g. (0J0 mole) of ethyl bromide and 12 j. (OJO g. ce of lithium metal. The yield of tetrapfacnyUhne was atom) of -- r~ 'na tsraaags. The reactiou mixture wax 7.0 g. (0j03 mole), m.p. 233-233*. The rendnsl Baud held at the r e d ttmptnbre hr ooe bowr, then hydrolysed waa dirtBled under vacuum, giving a 34-g. uixtma erf 1J- and worked up as described hi the above apsvacst. The dipbeuyletbena and benxylpfaenyhalane, which dbtiUcd pbcnybaae and ethjHbhexykdana obtained were con at 100-100* (0.43 am .). T bh m ixture was Created with verted to tetnpbesyWhae and ethyitripbenybilane, re an ether solution of pbenyQithhxa, which had been made spectively. The yirid ot tctrmphesylsflaae was 24.0 g. from 03 g. (0.40 mole) of bromobcuaene and an excess of 7(0X173 mole), m.p. 233-233*; that at tripbeoylctbyhilane lithium metaj. The reaction m ixture was hydrolysed and was JO g. (0X34 molt), n ^ . 73-73*.* The liquidremain, worked up in the usual manner. The ether was evaporated, ing after the separation of the pbenyfaQaae and ethylpbeayt- and the residual tkmid distilled under reduced prereere to h w waa d i m h d under reduced pressure, giving I2J g. of remove the 1,2-dipheaylethene. The residue was treated crude xym-dirthyidiphenyhiMoxane. (CUfsSiHCJf.M), db- with 20-- 10* petroleu m ether, which earned benxyhripbenyt- i.tlinf at 140-200* (OJOS mm.). The onde product was re sQxne to precipitate. This compound was recsystmlHaed distilled at 107* (0X3 m ) to obtain a sample far xn&Jytlr twice from 0 0 % ethanol; yield 15 g. (0-04 male), m.p. 00- euwj physical properties. The infrared spectrum at the 07*, coo.pound was Idcutlral with that" of an anthentic sample (TreTii e of 11m TVehiiiiiMiafh11saa bv U f i h n ihef- of r j m diethykliph>jyidisik)xane,a*D 1J23. u u m Hydride.--A4.OgT(0Xflmoie) s a m at Mim ifkihenyt- A mal. Caled, for CwHwOS: C. 07J; H, 7.75; mol. dixilaxane waa added dropw he to 2.0 g. (0.7male) at uthium wt., 236. Found: C.07X; H.7J0; mol.wt.,282. afamtnum hydride in 250 ml. of ether. SZigbt rpnmtwg of Clacvag* of syn-DTjhmyliJhlTnrsna by PSenjtmxgna- foraixxm Bromide.-- A 23-g.(0.10mole) sample ofijm dipbeayL dtsBoxane in 20 ml. of ether was added dropbe to a 200-ml. ether solution of pbcnyhnagnniuin bromide, which had been m a d e from 03 g. (0.40 mole) of bromobenxenc and 4J g. (0.40 g. atom) of magnesium turnings. The reaction mix ture waa held at the reflux temperature far ooe hour, then hydrolyzed and w orked up in the usual way. The ether was removed, and the residual timid fractionated. A the solvent resulted, and a heavy white predpitate formed. The reaction mixture was allowed to stand two hours and then it was poured oato m mixture of crechxd Ice end dilute hydrochloric add. The ether layer was separated, washed first with dilntf hydrochloric add and then with water, and dried over Dricrite. The ether was dbtiStd off and the product (2.1 g.,50%) distilled at 110* (740J mra.). The product was identified as pbenybilane by its point and infrared spectrum.1* Acknowledgment*.--Analyses were by Miss J.3.0- g. (0.03 mole) fraction composed of pbenylsilzne dis tilled at 118-120*. This compound was identified by its Dickey of the Indiana University Microonalytiealinfrared spectrum* and its boiling point. The residual Laboratory. This paper is based upon work perliquid was under redneed pressure. giving 21.7 g. formed under contract Nonr-90802 NR 356-321(0*004 mole) of dtphcnyhane, which dstilled at 60* (0.0 (Office of Naval Research).m m .). The dipbylsxlsne was identified by its infrared spectrum.1* A fraction coushtiof of 5.0 g. (0.014 mole) of 2.4.0- triphcoyIcyclotritfloxanc, (C*HJ*HO),. distilled at (18) C. Haac ir t C. Haaw, Tan J o o u u , T4, ItM (1U3). 108* (0.02 mm.), a*u 1-500; caled, mol. wt. 300, foasd 352. The infrared spectrum of this compound was identical Bloomimcton, I ndiana N 0 T C P T h is ----------------- ^ p ro te c te d by e o p y r..5rf.;aj,/ (Contribution r a o n the C kxkxcal L abora to r o r I owa S t a ts C o l l e g e ! H fllogcn D erivatives of D ibenzo-p-dioxin By H enry G ilkan and J oseph J . D ietrich R kcxiyxd1O ctober 16, 1050 IcbiVmb^cJ2ncTcomotXlrrlbouo)Scp-uSdtnl.mtiiIocbvnapcefsornlJelxadpobmrlae-ybrpclag-olntdoiwixvtoooAeniyxnr-sieujeciifl-fotddo(r.VimrotIreh2Imte-)hc;o(hapldlrr)oeser.paoirna-ercIal(IrutI,eidIopl)enov.dr.ot2aef.vld7ol2.-n.d.~gbiVcrTwholhlmIioeIthrooal--a-ndbdir(bboIreImIienXIo)fz,-otadh.2ri^eeb.7doc-inrnodeexixtwboiiccn-apctmlo~(Vmdidoi'i)op-scxoa(uiunVnsndsid(i)oslon.\af'n)dVdSeaIatnI2rl.dui.n3Hcg.t71bu.ewr8he.i^tt-fhrpKotrrrxoVmalooIbef,-rsddoVimfbfoIcrIoron-maxtdhnoieb-dIpsene-VnedxxeiIaopnIKI.ed.nm-s2diJviBUo-erxdAii*elnJ-f- theStuddibieems oon-p-thdeiooxirnien(tIa)tionnucole(uesnthearivneg-legdroutopstohne cporenpfiarrmataitoionnooffathneuimr sbterruoctfuhraeJso.gen derivative* and 14-40 H kXXT G CLOAK AXD JOSSTH J. 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M arch 20, 1957 H alookx.D sarv aT iv n o r D kkxo^-dioxtk 1441 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