
%0 Journal Article
%A Coxon, JM 
%A Steel, PJ 
%T A study of cations generated from 1- and 3-methyl- and 1,3- and 1,7-Dimethyl-2-arylbicyclo[2,2,1]heptan-2-ols
%J Australian Journal of Chemistry
%D 1980/11/01
%V 33
%N 11
%P 2455-2466
%K 
%R https://doi.org/10.1071/CH9802455
%U https://www.publish.csiro.au/paper/CH9802455 
%X The 13C n.m.r. spectrum of the 2-(4?-methoxyphenyl)-1- methylbicyclo[2,2,1]hept-2-yl cation is reported and indicates a significant reduction in &#960;-delocalization of charge into the aryl ring on introducing a C1-methyl group. The endo-3-methyl-2- phenylbicyclo[2,2,1]hept-2-yl cation in strong acid undergoes epimerization at C3 and does not afford the tetracyclic or dimeric compounds. 1,exo-3-Dimethyl-endo-2-phenylbicyclo[2,2,1]heptan-exo-2-ol on reaction with HSO3F gave the exo-3,endo-6-dimethyl-2- phenylbicyclo[2,2,1]hept-2-yl cation at temperatures above -50&#176;. This is the first alcohol containing a C1-methyl, C2-aryl system which does not undergo a WM; 6,2H; WM rearrangement. Reaction of 1,syn-7-dimethyl- endo-2-phenylbicyclo[2,2,1]heptan-exo-2-ol gave the parent 1,syn-7-  dimethyl cation which at -50&#176; gave the exo-5,endo-6-dimethyl-2- phenylbicyclo[2,2,1]hept-2-yl cation but not the WM; 6,2H; WM product. The structural features which determine the pathway of rearrangement of these bicyclic cations are discussed. 
