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

Abstract

The 13C and n.m.r. spectra of a series of 2-aryl-3, 3-dimethylbicyclo[2, 2, 1]hept-2-yI 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, l]hept-2-yl cations in fluorosulfonic acid give substituted 7, 8-dimethyltetracyclo- [7, 4, 0, 02, 7, 04, 8]trideca-l(9), 10, 12-trienesulfonyl fluorides. Substituted 7, 8-dimethyltetracyclo[7, 4, 0, - 02, 7, 04, 8]trideca-1(9), 10, 12-trienes and 7, 8-dimethyltetracyclo[7, 4, 0, 02, 7, 04, 8]trideca-1 (9), 10, 12-triene were prepared from 2-aryl-3, 3-dimethylbicyclo[2, 2..