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- Title
Synthesis and structure of products of hydroxylamine acylation with 3-carboxy-2,2,5,5-tetramethylpyrrolinoxyl derivatives.
- Authors
Sen', V. D.; Shilov, G. V.; Golubev, V. A.
- Abstract
The reaction of NH2OH with the derivatives of 2,2,5,5-tetramethylpyrrolin-1-oxyl-3-carboxylic acid in all events led to the formation of a mixture of the corresponding nitroxylhydroxamic acid with a stable O-acylhydroxylamine. The ratio between the products depends on the nature of the acylating agent and under the studied conditions varies from ∼5.5: 1 to 1: 3 indicating the comparable nucleophilicity in this reaction of N and O atoms in the hydroxylamine. The most active chloride of the mentioned acid alongside the indicated products afforded in a considerable yield N,O-diacylhydroxylamine and the triacylated hydroxylamine, 3-{[(2,2,5,5-tetramethyl-1-oxylopyrrolin-3-yl)carbonyloxyimino][(2,2,5,5-tetramethyl-1-oxylopyrrolin-3-yl)carbonyloxy]-methyl}-2,2,5,5-tetramethylpyrrolin-1-oxyl. The structure of both latter compounds was established by XRD analysis.
- Subjects
CHEMICAL reactions; CARBOXYLIC acids; ORGANIC acids; RING formation (Chemistry); ABDERHALDEN reaction
- Publication
Russian Journal of Organic Chemistry, 2009, Vol 45, Issue 8, p1189
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428009080132