Reactions of 2, 3-dimethylenebutadiene dianion with electrophiles. Synthesis and conformations of 2, 3-disubstituted-1, 3-butadienes

RB Bates, B Gordon III, TK Highsmith…

Index: Bates, Robert B.; Gordon, Bernard; Highsmith, Thomas K.; White, James J. Journal of Organic Chemistry, 1984 , vol. 49, # 16 p. 2981 - 2987

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Citation Number: 30

Abstract

Reactions of 2, 3-dimethylenebutadiene dianion 1 with monofunctional electrophiles were found to provide the best routes to symmetrically substituted 1, 3-butadienes such as 2c-n. Evidence that at least some of these reactions go by single electron-transfer mechanisms is presented. Possible mechanisms for the formation of some unusual byproducts are discussed. Reactions of 1 with dichlorides and dibromides were found to provide the best ...