A study of methyl-substituted 2-Arylbicyclo[2,2,1]hept-2-yl cations
JM Coxon, PJ Steel, JM Coddington, ID Rae and AJ Jones
Australian Journal of Chemistry
31(6) 1223 - 1233
The 13C and 1H N.M.R. spectra of a series of 2-aryl-1,7,7- trimethylbicyclo[2,2,1]hept-2-yl cations generated in strong acid at low temperature are reported. These cations reorganize at higher temperatures to 2-aryl-5,5,endo-6-trimethylbicyclo[2,2,1]hept-2-yl cations, thereby relieving the unfavourable C 1 methyl-C 2 aryl steric interaction present in the parent cations. At higher temperatures the bicyclic skeletons collapse to monocyclic allylic cations.
Full text doi:10.1071/CH9781223
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