The chemistry of terpenes. Part VI. Reactions involving the isomeric pinan-10-yl carbonium ions

Abstract

The relative yields of rearranged and unrearranged products obtained from the isomeric pinan-10-yl ions, produced during the deamination and deoxidation of the isomeric 10-aminopinanes and pinan-10-ols respectively, are compared with the yields of corresponding products resulting from methanolysis of the pinan-10-yl tosylates. The similarities and differences are rationalized in terms of the formation of ‘free’ and solvated ions and of ion pairs.