Reaction of 1, 1-diphenyl-2-vinylcyclopropane with tetracyanoethylene, diene, diborane, and dibromocarbene. Formation of unusual adducts after rearrangements …

N Shimizu, T Fujioka, S Ishizuka, T Tsuji…

Index: Shimizu,N. et al. Journal of the American Chemical Society, 1977 , vol. 99, # 18 p. 5972 - 5977

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Citation Number: 13

Abstract

Abstract: 1, l-Diphenyl-2-vinylcyclopropane (la) reacts with tetracyanoethylene yielding N- diphenylmethylene-2, 3, 3-tricy-ano-5-vinylcyclopent-1-enylamine (2a) as a major adduct. The related ethylene IC produces fluorenylideneamine 2c and the chain adduct 4a. The expected cycloadducts did not form in both cases. In contrast, the Diels-Alder reaction of la with tetrachlorocyclopentadienone ethylene acetal gives the normal cycloadduct 6c. ...