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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

The Reaction between Acetone and Ammonia. II. Isomeric Oximinoketones related to Diacetoamine

NC Hancox

Australian Journal of Scientific Research 3(3) 450 - 460
Published: 1950

Abstract

The compound 2,2,4,4,6-pentamethyltetrahydropyrimidine hydrate, formed in the reaction between acetone and ammonia at room temperature: is converted by nitrous acid to the 5-oximino derivative in 30 per cent. yield. This oxime is decomposed by acid under mild conditions to give acetone, ammonia, and the salt of 4-amino-4-methyl- 2,3-pentanedione 3-oxime. More vigorous acid treatment of the cyclic oxime, or reaction of the open-chain 3-oxime with boiling dilute acid, causes a migration of the oximino group to the 2 position. Evidence is adduced to show that the 2-oxinze has the α- (anti) configuration, whereas the 3-oxime has the β- (syn) configuration.

https://doi.org/10.1071/CH9500450

© CSIRO 1950

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