
TY  - JOUR
A1  - Brown, RFC 
A1  - Coddington, JM 
A1  - Coxon, JM 
A1  - Jones, AJ 
A1  - Rae, ID 
A1  - Steel, PJ 
T1  - A study of cations generated from 1-Methyl- and 7,7-Dimethyl-2-phenylbicyclo-[2,2,1]heptan-2-ols
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1978
VL  - 31
IS  - 12
SP  - 2727
EP  - 2735
KW  - 
UR  - https://doi.org/10.1071/CH9782727 
N2  - 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. 
ER  -

