137724-75-5Relevant articles and documents
Reactions of Cyclohexane Derivatives in Superacids
Dean, Christopher,Whittaker, David
, p. 1541 - 1543 (2007/10/02)
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.