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Synlett 1992; 1992(2): 133-134
DOI: 10.1055/s-1992-21291
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Reaction of α-Sulfonyl Carbanions with Electrophilic Monohalogenocarbenoids: A New Wittig-Like Formation of Alkenes

Carmen De Lima* , Marc Julia, Jean-Noël Verpeaux
  • *Laboratoire de Chimie de l'Ecole Normale Supérieure, 24 rue Lhomond, F-75231 Paris Cedex 05, France
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Publication Date:
08 March 2002 (online)

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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.

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