Abstract

Reaction of adamantylidene and phenylcarbene with ethylthiol, ethylene dithiol, allylethylsulfide, allylphenylsulfide, and trimethylenesulfide involves the formation of a sulfur ylide intermediate, followed by H-migration, 2,3-sigmatropic shift, or ring opening to give sulfides. The sulfur ylide formed in the reaction of phenylcarbene with trimethylenesulfide is directly observed by laser flash photolytic techniques.

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