Document pBLQOqmm3eVrM8k3eJxvwv4Qw

March 20, 1957 Halogen D erivatives of Dibenzo-P-dioxin 1439 tinned abnve ws added dropwwe to a 300-ml. ether solutioa pheny llithiurn, which bad been made from n o c. (0.70 mole) of bromobenxenc nn n excess of Litbruir metal. A fter re during for ooc boor, this reactioa mixture wax p o u n d , onto cracked Ice and dilate sulfuric acid to destroy th e races TbenyUrthium. The ether waa then removed by evaporation, leaving a white soUd, which waa collected and d rie d . This solid waa placed in a S ublet extractor and ex tra c te d for ooe boor with 20-40* petroleum ether to dis with that of the sample of the trimer obtained by the hy droAlmysoiJs. of pbeoylbromosilanc. Calcd. for CH/3Si: C, 50.0; H, 4.95. Found: C.C5l9ea.9v;agHe ,of5sXym0.-DiakomyWisilarana by Benxjlmaraeefana Chloride.--A 23-g. (0.10 mole) sample of ryw -diphari- disilaxanc in 25 ml. of ether waa added dropwise to a 3 u ^ ml. ether sofutioa of benxyhnagnesium chloride, which hod solve th e methyhripbenybflanc (derived from the metby1- been made from 63 g. (0X 0 mole) of beuxyl chloride aad 12 phenylailane). The yield of this compound waa 7.0 ( . g. (OX g. atom) of magnrsinm turnings. T bt reaction ( 0 .0 3 m ole), m .p. 6 5 -6 6 * ." The remainbig solid waa ex started immediately and refluxing of tha solvent rsauitad. tra c te d with tokaenc for 13 boon to give 33-0 g. (0.10 mole) The reaction mixt ure waa bdd a t the reflux temperature far of letrapbenybilane (derived from phesyiulane), m.p. 232- ooc boor, then hydrolysed and worked up in the usnal man sfB2ro3iorlh3Coomi*xnltea.id"ao7ad0vaeaaa.gig--nt.ee5(A0dt0h-45ymio0hyl-nm.mgaa.gotD(nle0eteyt)Jshhah0eatnraaemywtihboadralyieoala)mddbaaidrgadoemaemdn,piawdlderehbeiayacythnEdsathyhnam1yd2timdobfi.peaaegb(n2n0c0-aam05ey-0flamaddmgiie-.. ner. T bt ether was off and a 19-g. ailaunt of pbenybolane and tolurm disffflrd a t 120*, fcavfag a residua which waa distilled later. Tba m Utins of phenyfcflhaa and tmolaudeenefrowmaa94trega.te(0dXw0 imtholpeh)easyt Uhzuthniuoihn,a wkkJa bad t w a i and an *- ccn of lithium metal. The yield of tctrapbeuyUane wna atom ) of tunings. The reaction mature waa 7.0 g. (0X 3 mole), m.p. 233-233* . Tba resUnal Squad he id a t the reflex temperature for one bonr, then hydrolysed was dhtfllrd under vacuum, giving a 24-g. uihrtnre cf 1,3- an d worked up as described ia the above experiment. The dipbenykthanc aad bcaxylpbenyinlaae, which distilled pbcnytsilaae and ethjHbhenykdaaa ofttaiard were coo- at 106-160* (0.43 m m .). This mixture was treated with -(wtvsa0peag-ers0tca7e7tf3idtJveOmertlgoyto.h.l(eet0)es,XTtermhp3aae4p.rpbam.yetfino2ocy3lined3k)-,au2atsa3attn3h.ep*et,e;pat7xfa3atad-Wes7nh3cye*tUhaa.*yytkflntrcrieTrihpiabpabncbeedesSsywcqyltuaebhiatyidhllayrp2neb4hemO.e,0naaiyrnneglc--. an ether solutioa of pbeayUfthlum, which had been made from 63 g. (0 .4 0 mole) of bromobenxene aad an w v w of lithium metal. The reaction mixture was hydrolysed sad worked up la the usual manner. The ether was evaporated, and tba residual Squid * under reduced p r a a n to h iw waa distilled wader radweed p r a a s t , firing I2X f . of remove tbe 1,2-dipoenyirthaae. The residua was treated crude ry as dirthykUpbenykflaariiaiif , (&H*SiHCtH)rO, da- with 20-40* petroleum etber, which caused benxyltripbeny^ tilling a t 140-200* (0X 6 m m .). The crude product waa re ilaac to precipitate. This compouod was recrystalHsed distilled a t 107* (0X 3 mm.) to obtain a sample for analysis twice from 9 5% ethanol; yield 15 g. (0X 4 mole), m .p. 9 6 - nad physical propaties. The infrared spectrum of the 0 7 \ * coenpoond was identical with that* of an anthentic mmplc of Afjn--a t .^ L ^hyMjphxtyMwnfmiie, Calcd. for C.*HQS,: a*D C, 1X23. 67.2; H , 7.75; mol. CtMvaga of iv--.plphsnytdlsHavas by ttmn Hytfrida.--A 4.0-g. (0X 2 mole) sample aLt krvhmh-mdipDbesnnydi-- dtsilaxane was added dropwbe to 2 .0 g. (0 .7 mole) of tfehlua w t., 2 8 6 . Found: .C ,67X ; H , 7.00; mol. w t., 282. aluminum hydride in 250 ml. of etber. Slight *w*" *"g of Clacrago of rym-DIphan anxm Bromide.--A 23-g. (0 .1 0 jldhfloim mole) mm pibeyofPs bj mesdyitpmbiegoMyl-- disfloxane in 20 ml. of ether was added dropwise to a 200-ral. ether sohttion of pbenyhnagn rn im bromide, which had been made from 63 f . (0 .4 0 mole) of bromobenxene and 4.8 g. (0 .4 0 f . atom) of magneaaun turnings. The reaction mix tu re was held a t the reflux temperature far ooe boar, then hydrolysed and worked op ia the nwtal way. The ether was removed, and the residual liquid fractionated. A 3 .0 - f . (0 .0 3 mole) fraction composed of pbeaylsilaae dis tilled a t 118-120*. This compound waa identified by its infrared spectrum14 and its hoiKng point. The residual liquid was.dwtiBed under reduced prnnure, giving 11.7 g. (0 .0 6 4 mole) of dtphenybOaoe, which distilled st 60* (0 .6 m m .). The dipbesylsUme was identified by its infrared tbe solvent resulted, and a heavy white pr edpitats farmed. The reaction mixture was allowed to stand for two hours and then it was poured onto a mixture of cracked lea and dilute hydrochloric ad d . The etber layer was separated, washed first with dilate hydrochloric acid aad water, aad dried over Drierite. Tbe ether was then woitSh and tbe product (2.1 g., 5 0 % ) distilled st 119* (740X m m .). Tbe product was identified as pbeaybiiane by hs boiling fLD(poOoariiAfcmbnfkitocceekaredyaanodtooofuwirfnnNylfdte.rbadaevergreaTmdlIchnesoRidpnsneeitatcsprnte.aar--aaucprmteAcUr.h1nN4n)ia.siolvynb*esrare-ss9sie0tdy8w0euM2rpeioHcnbrRoywanoM3ar5kli5ys-tps3ice2Jar1.l spectrum .1* A fraction consisting of 5 .0 g. (0X14 mole) of 2,4.6-tripbenylcycIotrisiloxane, (CJUSiHOh, distilled at (18) C. H ut, lM C. Hu m , Tan fo o u u , T4, ISM (Ittt). 168* (0 .0 2 m m .). a*n 1X66; calcd. mol. wt. 366, fooad 3 5 2 . The infrared spectrum of this compound was identical Bloomington, Indiana \ -Nb e o n E e? lec T te h is d by c o p y ,. ''# (CoxiaiBimoN ntoK the Chemical Labokato** op Iowa State College] . Halogen Derivatives of Dibenzo-p-dioxin B y H enry G ilman and J oseph J . D ietrich Recxiyed Octobu 15, 1956 ci*b(o<hVror5^lotmrDhnoryoobc)p-tudcwbfwirrbo_noeBc_oindipl_xaruoeibrnlpe-ybpoc-lg-airndtaiwMivitaoielioyx-nru/iei>enscf-l_otdd(fr.waVm^txeIb2m0te-nco(hapIdIr)roeaer.poina-rciall(rut,UeidpoI)eonV,dr.to2aef,lVd7o2.-Tnd-g/bi'VcrTwohIhlmIioetIhrooml--a-dbdbb(roIerIIimneXIz)for,v-tahdp2reie-,b7doen-krdnee)ixxwtbimocr-acoplom(-Vmddoi)ip-socoia(uiunVnsndsId(i)oIsoVn.fa)ndVdSeaIatnI2rl.dui.n3c'tg.tbI7ueXwrbe-i2ttfh-peotrrrooVmaodbIefo.rsd-oVdmffioIrbIoroe-matmdhniedbbs-eea>Vnp^xaIeboaIIsad-.^taidlivXiB(ovU-rxdiCm#elT--f theStuddibieenszoon-pt-hdejooxrinien(tIa)tionnucolefuesnthearvineglegdroutopsthone cporenpfiarrmataitoionnooffathneuimr sbterrucotfuhraelso.gen derivatives and 1440 H etvxt Gilman and Joaara J. DirrxiCB Vol. 78 TI ~ 4 . 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M arch 20, 1957 Halooek Dmltyattv** or Daxio-^-DioxiK 1441 B xpecinw ttaP 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