Synthesis 2005(7): 1077-1082  
DOI: 10.1055/s-2005-861836
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Chemistry of N,N-Bis(siloxy)enamines. Part 8. [1] A General Method for the Preparation of α-Azido Oximes from Aliphatic Nitro Compounds

Alexey Yu. Sukhorokov, Igor V. Bliznets, Alexey V. Lesiv*, Yulija A. Khomutova, Yuriy A. Strelenko, Sema L. Ioffe*
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Leninsky prosp. 47, Russian Federation
Fax: +7(95)1355328; e-Mail: iof@ioc.ac.ru;
Further Information

Publication History

Received 14 December 2004
Publication Date:
21 February 2005 (eFirst)

Abstract

A new strategy for the synthesis of α-azido oximes from aliphatic nitro compounds via interaction of N,N-bis(silyl­oxy)enamines with trimethylsilylazide was realized to give the target products with good yields.

    References

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19

The derivatives 3 can be purified via rectification in vacuo or after filtration through silica gel. The treatment of thus purified intermediates 3 with methanol gave rise to azido oximes 2 in quantitative yields without any purification.

20

The attempts to preparate oximes 2 from ANC without isolation of BENA 1 failed.