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.