Jump to main content
Jump to site search

Issue 10, 1991
Previous Article Next Article

Reactions of cyclohexane derivatives in superacids

Abstract

The reactions of menthol with FSO3H–SO2 and neomenthyl chloride with SbF5–SO2ClF follow different routes. The first yields a substituted cyclopentyl cation and the second a substituted cyclohexyl cation. Experiments on substituted cyclohexyl chlorides show that replacement of all the hydrogen atoms on the next but one carbon atom to the reaction centre blocks formation of a carbocation. It is suggested that ionisation of an equatorial chlorine atom takes place with assistance from an intramolecular electronic interaction, forming the methyl cyclopentyl carbocation in a synchronous process, rather than stepwise via the cyclohexyl carbocation. Reasons for contrasting behaviour in solvolytic reactions are discussed.

Back to tab navigation

Article information


J. Chem. Soc., Perkin Trans. 2, 1991, 1541-1543
Article type
Paper

Reactions of cyclohexane derivatives in superacids

C. Dean and D. Whittaker, J. Chem. Soc., Perkin Trans. 2, 1991, 1541
DOI: 10.1039/P29910001541

Search articles by author

Spotlight

Advertisements