BRIDGED POLYCYCLIC COMPOUNDS .50. SYNTHESIS REARRANGEMENTS AND REACTIONS OF SOME DIBENZOBICYCLO[3.2.2]NONATRIENES AND DIBENZOTRICYCLO[3.3.1.0]NONADIENES

Addition of the dichlorocarbene precursor phenyl(trichloromethyl)mercury to dibenzobicyclo[2.2.2]-octatriene (1) leads to 3,3-dichloro-6,7;8,9-dibenzotricyclo[3.2.2.02.4]nonadiene (2). Thermal rearrangement of 2 gives 3,4-dichloro-6,7;8,9-dibenzobicyclo[3.2.2]nona-2,6,8-triene (3). Rearrangements between this system (derivatives of A), the 2,3;8,9-dibenzobicyclo[3.2.2]nona-2,6,8-triene system (derivatives of B), and the 3,4;6,7-dibenzotricyclo[3.3.1,02,8]nona-3,6-diene (derivatives of C) system have been studied in a preliminary fashion. The rearrangements available in these systems involve allylic, Wagner-Meerwein, and homoallyl-cyclopropylcarbinyl, and our results appear consistent with classical cation intermediates. Pmr spectral correlations and synthetic procedures for a number of new compounds are reported. © 1968, American Chemical Society. All rights reserved.