Halogenation of enol tautomers of 2-cyanoacetamide and malonamic acid

A Eberlin, DLH Williams

Index: Eberlin, Alex; Williams, D. Lyn H. Journal of the Chemical Society, Perkin Transactions 2, 2002 , # 7 p. 1316 - 1319

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Citation Number: 10

Abstract

Reactions of 2-cyanoacetamide (CA) with both bromine and iodine at low halogen concentration in aqueous acid solution were first order in halogen and CA, consistent with an interpretation involving rate-limiting halogenation of the enol tautomer. There was no acid dependence in the range 0.1–0.5 mol dm− 3. The observed rate constants for bromination and iodination were very similar, indicating that both probably occurred at the encounter ...