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

Andrey A. Tabolin; Alexey V. Lesiv; Sema L. Ioffe

doi:10.1055/s-0029-1216907

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Synthesis 2009(18): 3099-3105
DOI: 10.1055/s-0029-1216907

PAPER

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

Andrey A. Tabolin, Alexey V. Lesiv*, Sema L. Ioffe
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, 119991 Moscow, Russian Federation
Fax: +7(499)1355328; e-Mail: lesav@mail.ru;

Further Information

Publication History

Received 16 April 2009
Publication Date:
14 July 2009 (online)

Abstract
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Abstract

The reactions of N,N-dioxyenamines with carboxylic and sulfonic acid anhydrides were investigated. A new method for the synthesis of α-hydroxyoxime derivatives via the reaction of N,N-dioxyenamines with trifluoroacetic anhydride is described.

Key words

1,2-oxazine - trifluoroacetic anhydride - hydroxyoxime - enamine - rearrangement

References

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13

For BENA nucleophilicity parameter N = 3-5 according to Professor Mayr’s scale, while for ‘classical’ enamines N = ≥ 11 (ref. 4).

17

Mikhailov, A. A.; Lesiv, A. V.; Ioffe, S. L. unpublished.

19

For discussion of the stereochemistry of the rearrangement of 2 see ref. 16.