A Novel Cyclopropanation

Author:

Bostick TM,Christie SD,Connolly TJ,Copp S,Langler RF,Reid DL,Zaworotko M

Abstract

Reaction between benzaldehyde and methyl α- benzylsulfonylacetate furnishes methyl (E)-α- benzylsulfonyl-β-phenylacrylate as the exclusive Knoevenagel adduct. The related condensations between α-benzylsulfonylacetonitrile and paraformaldehyde furnish trans-1-benzylsulfonyl-2-phenylcyclopropane-1-carbonitrile in modest yields. These product structures are established by X-ray crystallographic analysis. Phenylsulfene is ruled out as an intermediate in the formation of the cyclopropane.

Publisher

CSIRO Publishing

Subject

General Chemistry

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