EVALUATION OF THE ?-CONJUGATIVE EFFECT OF THE 2-METHYLENE AND THE 2-OXO SUBSTITUENT ON THE STABILITY OF CARBOCATIONS IN THE SOLVOLYSIS OF BICYCLIC BRIDGEHEAD DERIVATIVES

Article abstract of DOI:10.1016/S0040-4039(00)82470-3

The incipient 2-methylenebicyclo<3.2.2>non-1-yl cation is stabilized by allylic conjugation by 4 kcal/mol compared with the more rigid 2-methylenebicyclo<2.2.2>oct-1-yl cation.In contrast to this, no appreciable stabilization due to carbonyl ?-conjugation