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;
1987-01-01
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.
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