Reaction of α-Sulfonyl Carbanions with Electrophilic Monohalogenocarbenoids: A New Wittig-Like Formation of Alkenes

Abstract

Various α-sulfonyl carbanions were treated with chloromethyl- or iodomethylmagnesium chloride or 1-chloropentylmagnesium chloride solutions, leading to substitution of the sulfonyl group by a methylene or pentylidene moiety, respectively. This new olefin formation reaction indicates that monohalogenocarbenoids are strong electrophiles; it is shown here that magnesiated chloropentane is indeed more electrophilic than chloropentane itself.