The Journal of Organic Chemistry

Conformations of the Radical Anions from Dialkyl Maleates and Fumarates

S Nelsen, J Gillespie

Index: Nelson,S.F.; Gillespie,J.P. Journal of Organic Chemistry, 1975 , vol. 40, # 16 p. 2391 - 2394

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Citation Number: 13

Abstract

Both dialkyl maleates and fumarates give the same mixture of monoanion radicals, as several workers have noted. It is proposed that all the conformations observed are trans at the original carbon-carbon double bond, and that syn and anti alkyl conformations are observed with primary alkyl groups. This proposal requires that surprisingly slow carbonyl carbon-alkoxy1 oxygen rotation occurs in the radical anions.