Bridged polycyclic compounds. 88. Multiple intermediates in solvolysis of certain bridged bicyclic and tricyclic compounds.

Article abstract of DOI:10.1139/v86-180

Acetolyses of 7-chloromethyl- and 7-bromomethyldibenzobicyclo<2.2.2>octatrienes, 8-chloro- and 8-bromo-7-methylenedibenzobicyclo<2.2.2>octa-2,5-dienes, 4-bromo-8-methylenedibenzobicyclo<3.2.1>octa-2,6-diene, and 2-chlorodibenzotricyclo<3.2.2.0^2,4>nonadiene were carried out.The results observed were consistent with the involvement of two carbocations interconverting by a Wagner-Meerwein rearrangement, and with the absence of the 1-dibenzosemibullvalenylcarbinyl cation, which is the cyclopropylcarbinyl isomer of one of the cations produced.The preparations of the reactants and products are described.