Spectroscopic characterization of triplet 4, 5-benzocycloheptatrienylidene

JE Chateauneuf, KA Horn…

Index: Chateauneuf, John E.; Horn, Keith A.; Savino, Thomas G. Journal of the American Chemical Society, 1988 , vol. 110, # 2 p. 539 - 545

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Citation Number: 17

Abstract

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 ...