The alkylation followed by the deselenenylation of cyanomethyl phenyl selenide (1) gave α,β-unsaturated nitriles. The method was applied to generate 1-cyanocyclopropene, which was trapped using anthracene.
Treatment of the title compound with n-butyllithium produces the lithiomethylene derivative (4) . The reagent 4 so generated has been shown to serve effectively as an equivalent of the formyl anion by alkylation of 4 with alkyl halides followed by hydrolysis with mercuric ion to the corresponding aldehyde.
The reaction of dimethylsulfonium phenacylide 1 with malononitrile gave C-phenacylated compound. The reaction of 1 with acetylacetone or ethyl acetoacetate led to dihydrofuran derivatives via O-phenacylation followed by cyclization.
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