Journal article

A study of cations generated from 1-Methyl- and 7, 7-Dimethyl-2-phenyIbicyclo[2, 2, l]heptan-2-oIs

RFC Brown, JM Coddington, JM Coxon, AJ Jones, ID Rae, PJ Steel

Australian Journal of Chemistry | Published : 1978

Abstract

Attempts to generate the 1-methyl-2-phenylbicyclo[2,2,1]hept-2-yl cation (6) by reaction of 1-methyl-exo-2-phenylbicyclo[2,2,1]heptan- endo-2-ol (5) with HSO3F in SO2ClF were not successful, due to spontaneous rearrangement to endo-6-methyl-2-phenylbicyclo[2,2,1]hept- 2-yl cation (7). This cation (7) itself rearranges at higher temperatures to exo-6-methyl-2-phenylbicyclo[2,2,1]hept-2-yl cation (10) probably by a double Wagner-Meerwein rearrangement involving the intermediacy of 3-methyl-1-phenylbicyclo[3,1,1]hept-2-yl cation (11). The 7,7-dimethyl-2-phenylbicyclo[2,2,1]hept 2-yl cation (13) has been generated and shown to rearrange to 5,5-dimethyl-2- phenylbicyclo[2,2,1]-hept-2-yl cation (1..

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