Reactions of spiro [2.4] hept-4-ene derivatives with tetracyanoethylene. Extensive rearrangements involving aza-Cope process

…, N Asanuma, M Murakami, T Tsuji, T Imai

Index: Nishida, Shinya; Asanuma, Naoki; Murakami, Masashi; Tsuji, Takashi; Imai, Toshiro Journal of Organic Chemistry, 1992 , vol. 57, # 17 p. 4658 - 4663

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Citation Number: 8

Abstract

In CH2C12 or CH, CN, 1, l-dicyclopropylspiro [2.4] hept-4-ene (4a) reacted readily with TCNE in a unique manner to give 4-[N-(dicyclopropylmethylene) amino]-6-methylenebicyclo [3.3. 0] octJ-ene-2, 2, 3-tricarbonitrile (sa), an imine after extensive rearrangements, and 3, 3- dicyclopropylspiro [4.4] non-6-ene-l, l, 2, 2-tetracarbonitrile (Sa), a [, 2+, 2] cycloadduct. In the reaction of l-cyclopropyl-l-methyl derivative 4b, 3-(1, 1, 2, 2-tetracyanoethyl)-~-(2- ...