Journal of the American Chemical Society

Facile heterolysis of a carbon-carbon bond. Arylazodicyanomethanides as the leaving group capable of generating tert-cumyl cation and the hydrogen-bond- …

T Mitsuhashi

Index: Mitsuhashi Tsutomu Journal of the American Chemical Society, 1986 , vol. 108, # 9 p. 2394 - 2400

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Citation Number: 17

Abstract

Abstract: Decompositions of (p-nitropheny1) azo-terr-cumylmalonitrile in polar solvents were found to proceed via the heterolysis of a carbon-carbon bond to generate tert-cumyl cation and the conjugate base of (p-nitropheny1) hydrazonomalononitrile. The major products arising from tert-cumyl cation are as follows: tert-cumyl methyl ether in methanol, the N- cumylpyridinium hydrazonide in pyridine, and a-methylstyrene in M e 3 0 and in DMF. The ...