Abstract
Seventeen new gem-dihalocyclopropyl-substituted derivatives of carbon, silicon, germanium and tin have been prepared by the Doering-Hoffmann or the phenyl(trihalomethyl)mercurial procedures from allylic and vinylic compounds of these elements. The reaction of vinyltrimethyltin with phenyl(bromodichloromethyl)mercury (to give 2,2-dichlorocyclopropyltrimethyltin) was complicated by a side reaction in which the phenylmercuric bromide formed cleaved the vinyl group from tin. The H2PtCl6-catalyzed addition trichlorosilane to 1,1-dichloro-2-vinylcyclopropane gave the expected 1,1-dichloro-2-(β-trichlorosilylethyl)cyclopropane, but thermal addition of trimethyltin hydride to this olefin apparently proceeded via a radical chain mechanism to give the ring-opened product. Me3SnCH2CH=CHCH2-CCl2H.
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