Abstract: 4, 5-Benzodiazocycloheptatnene (6) has been prepared by the low temperature nickel peroxide oxidation of the hydrazone of 4, 5-benzotropone. Thermolysis of 6 in benzene produces 4, 5-benzocycloheptatrienylidene (1) which undergoes a facile carbene- carbene rearrangement to yield 2-naphthylcarbene (2) as evidenced by the formation of 7-(2- naphthyl) cycloheptatriene (8). Irradiation of 6 in a 2-methyltetrahydrofuran matrix at 4 K ...
