The oximation of acetyl(hydroxyimino)acetone (1) with hydroxylamine affords a mixture of oxime derivatives. The products obtained by the action of an equimolar amount of hydroxylamine on (1) are the two 3,5-dimethyl-5-hydroxy-4-hydroxyimino-2-isoxazoline isomers (3a and b). The main products obtained by the action of an excess of hydroxylamine on (1) are two pentane-2,3,4-trione trioxime isomers (4a and b) and a little amount of 4-acetyl-3-methylfuroxan oxime (5). N.m.r. and chemical data of all these derivatives are discussed in order to determine both structures and configuration. X-Ray analysis of (3a), (4a), and (5) are also reported.

OXIMATION OF ACETYL(HYDROXYIMINO)ACETONE - NUCLEAR-MAGNETIC-RESONANCE SPECTROSCOPIC, CHEMICAL, AND X-RAY CRYSTALLOGRAPHIC STUDIES OF THE REACTION-PRODUCTS

FRUTTERO, Roberta;CALVINO, Rosella;GASCO, Alberto;AIME, Silvio;GOBETTO, Roberto;
1987

Abstract

The oximation of acetyl(hydroxyimino)acetone (1) with hydroxylamine affords a mixture of oxime derivatives. The products obtained by the action of an equimolar amount of hydroxylamine on (1) are the two 3,5-dimethyl-5-hydroxy-4-hydroxyimino-2-isoxazoline isomers (3a and b). The main products obtained by the action of an excess of hydroxylamine on (1) are two pentane-2,3,4-trione trioxime isomers (4a and b) and a little amount of 4-acetyl-3-methylfuroxan oxime (5). N.m.r. and chemical data of all these derivatives are discussed in order to determine both structures and configuration. X-Ray analysis of (3a), (4a), and (5) are also reported.
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II
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523
529
furoxans; oximes; oximation reaction; synthesis; NMR
Fruttero, Roberta; Calvino, Rosella; Bruno, Ferrarotti; Gasco, Alberto; Aime, Silvio; Gobetto, Roberto; Giacomo, Chiari; Gianluca, Calestani
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2318/111372
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