Synthesis

Reaction of N, N-Dioxyenamines with Anhydrides of Carboxylic and Sulfonic Acids; A New Method for the Synthesis of α-Hydroxyoxime Derivatives

AA Tabolin, AV Lesiv, SL Ioffe

Index: Tabolin, Andrey A.; Lesiv, Alexey V.; Ioffe, Sema L. Synthesis, 2009 , # 18 p. 3099 - 3105

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Citation Number: 10

Abstract

N,N-Dioxyenamine 2a was chosen as the model substrate owing to its relative stability. It was treated with various anhydrides leading to the formation of a mixture of cyclic oxime ethers 6-9 in moderate yields (Scheme [²] , Table [¹] ). No traces of alkylnitronates 5 expected to be formed in the case of C-attack could be detected in the reaction mixture. The most improved result was obtained in case of reaction with trifluoroacetic anhydride (Table [¹] , entry 2). ...