Issue 22, 1992

Alkyl migration in competition with phenylthio migration in the acid-catalysed rearrangement of alcohols

Abstract

Sulfonate derivatives of conformationally rigid syn-2-phenylthiocyclohexanols, which are prevented from phenylthio migration by stereochemistry, rearrange slowly by alkyl migration or ring contraction. In contrast to other electronegative groups, phenylthio slows the reaction down but allows migration of other groups.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1992, 3007-3013

Alkyl migration in competition with phenylthio migration in the acid-catalysed rearrangement of alcohols

M. Hannaby and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1992, 3007 DOI: 10.1039/P19920003007

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