Abstract
A variety of 2-mercapto-substituted vinyl radicals have been produced through the free-radical reaction of alkanethiols (including phenethyl, allyl, and benzyl mercaptans) with monosubstituted acetylenes in benzene at 90 o C. The 2-(benzylthio)vinyl radicals (6) readily rearranged to (vinylthio)methyl radicals (7) via a novel 1,4-migration of the phenyl group from thiomethyl to vinyl carbon; 2-(phenethylthio)vinyl radicals (12) underwent internal 1,5-hydrogen transfer to form β-thio-substituted benzyl radicals (13) which in turn suffered fast β-elimination of vi- nylthio radicals 18; and 2-(allylthio)-vinyl radical (20) underwent ki- netically preferred 5-exo cyclization to give the primary radical (26) which could easily rearrange to the more stable ring-expanded radical (25)
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