A study of the reactions of 2-Aryl-3,3-dimethylbicyclo[2,2,1]heptan-2-ols with acid

Abstract

The ¹³C and ¹H N.M.R. spectra of a series of 2-aryl-3,3- dimethylbicyclo[2,2,1]hept-2-yl cations generated in strong acid at low temperatures are reported. The chemical shifts of carbons proximate to the cation centres are discussed with reference to related cations. At higher temperatures, 2-aryl-3,3-dimethylbicyclo[2,2,1]hept-2-yl cations in fluorosulfonic acid give substituted 7,8-dimethyltetracyclo- [7,4,0,0^2,7,0^4,8]trideca-1(9),10,12-trienesulfonyl fluorides. Substituted 7,8-dimethyltetracyclo[7,4,0,-0^2,7,0^4,8]trideca-1(9),10,12-trienes and 7,8-dimethyltetracyclo[7,4,0,0^2,7,0^4,8]trideca-1(9),10,12-triene were prepared from 2-aryl-3,3-dimethylbicyclo[2,2,1]heptan-2-ols by reaction with perchloric acid under carefully controlled conditions.