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Synthesis 2005(7): 1077-1082
DOI: 10.1055/s-2005-861836
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
Further Information
Received
14 December 2004
Publication Date:
21 February 2005 (online)
Publication History
Publication Date:
21 February 2005 (online)
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.
Key words
aliphatic nitro compounds - azidotrimethylsilane - N,N-bis(siloxy)enamines - α-azido oximes
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References
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.
20The attempts to preparate oximes 2 from ANC without isolation of BENA 1 failed.