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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A study of cations generated from 1-Methyl- and 7,7-Dimethyl-2-phenylbicyclo-[2,2,1]heptan-2-ols

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

Australian Journal of Chemistry 31(12) 2727 - 2735
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 (14). At higher temperature, the bicyclic skeleton collapses to 3-isopropyl-1-phenyl-cyclohex-2-en-1-yl cation (15). These results demonstrate the structural requirements for cleavage of the 1,7-bond in the bicyclo[2,2,1]heptane skeleton.

https://doi.org/10.1071/CH9782727

© CSIRO 1978

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