Aromatization of 1, 4-cyclohexadienes with tetracyanoethylene: a case of varying mechanisms

BM Jacobson, P Soteropoulos…

Index: Jacobson, Barry M.; Soteropoulos, Patricia; Bahadori, Sheila Journal of Organic Chemistry, 1988 , vol. 53, # 14 p. 3247 - 3255

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Citation Number: 20

Abstract

The aromatization of 1, 4-cyclohexadiene and four alkyl-substituted 1, 4-cyclohexadienes with tetracyanoethylene was examined and found in four of five cases to involve two competing mechanisms. Most of each reaction proceeded by concerted ene addition followed by breakdown of the ene adduct, probably heterolytically. Rate constants for diene reaction were determined in acetonitrile-d, and p-dioxane-d8. Adducts were isolated in ...

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