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Original Articles

SYNTHESIS AND CONFIGURATIONAL STUDIES OF ARYL CYCLOPROPYL SULFONES

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Pages 297-305 | Received 06 May 1983, Accepted 05 Aug 1983, Published online: 19 Dec 2006
 

Abstract

The cycloaddition of arylthiocarbenes to styrene gave stereospecifically cis−1-(arylthio)-2-phenylcyclopropanes, which were subsequently oxidized to the corresponding sulfones. The cyclopropanation of α,β-unsaturated sulfones with dimethylsulfonium methylide yielded stereoselectively trans−1-(arylsulfonyl)-2-arylcyclopropanes. The configurational assignments of these compounds have been arrived at on the basis of IR and PMR spectral data. Chemical shifts for ring protons and other substituents reveal that all the substituents tend to cause protons cis to them to appear at higher fields than those trans to them. This has been used as a criterion to distinguish between cis and trans aryl cyclopropyl sulfones.

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