Isomerization of Hexamethyl(Dewar benzene) to Hexamethylbenzene Catalyzed by Electron Acceptors. Thermal Generation of an Exciplex

Article abstract of DOI:10.1021/ja00349a047

The reaction of hexamethyl(Dewar benzene) (HMD) with ground-state electron and with singlet and triplet excited electron acceptors reveals parallel behavior.The thermal acceptors catalyze the conversion of HMD to hexamethylbenzene (HMB) without formation of ions free in solution.The excited-state acceptors in some cases give ions, and in others only neutral ground-state products.The behavior of these electron acceptors is interpreted to indicate that formation of an exciplex in both the thermal and photochemical reactions initiates the process responsible for isomerization.In some cases electron transfer in the exciplex and dissociation lead to ionic products.