Nucleophilic substitution reactions of 4-t-Butyl-1-methylcyclohexanols

Abstract

The stereochemistry of the reaction of a number of nucleophiles with 4- t-butyl-1-methylcyclohexanol in the presence of acetic and sulphuric acids was studied. The stereoselectivity of the reaction found to depend on the size of the attacking nucleophile. Further evidence is presented for the existence of carbonium ion intermediates in the Ritter reaction.     In the series of 1-X-1-methyl-4-t-butyl derivatives with X = aryl, NHCOR, -CO-, NO₂, and NCl₂ the equatorial protons at C 2 and C 6 are markedly deshielded in the isomers where X is axial.