The Journal of Organic Chemistry

Reaction of organic anions. 166. Sigmatropic rearrangements of ammonium benzylides: new preparative and mechanistic aspects

A Jonczyk, D Lipiak

Index: Jonczyk, Andrzej; Lipiak, Dariusz Journal of Organic Chemistry, 1991 , vol. 56, # 24 p. 6933 - 6937

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Citation Number: 18

Abstract

(4) Ohno, K.; Tauji, JJ Am. Chem. SOC. 1968, 90, 99. K. Synlett 1991, 493. spectively. On the other hand, we postulate the [1, 4] sigmatropic rearrangement of the more stable ylide 3al'to account for the formation of product 6a (Scheme 111). The concerted mechanism is possible due to a six-electron aromatic transition state with suprafacial-suprafacial characteristics. 6i6 We have termed this type of reorganization of electron pairs as the" reverse" Sommelet- ...