89356-41-2Relevant articles and documents
Application of the Bucherer Hydantoin Synthesis to Diacetyl Mono-oxime. The Mechanism of the Bucherer Reaction, and the Constitution of the Hypothetical 'Dimethylbishydantoin' of Bucherer and Lieb
Bowness, W. Gary,Howe, Ralph,Rao, Balbir S.
, p. 2649 - 2653 (2007/10/02)
The major product obtained when the Bucherer conditions for hydantoin synthesis were applied to diacetyl mono-oxime was (3aRS,6aSR)-6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethylpyrroloimidazole-2,4-dione (3).Two minor products (7) and (9) are related to (3) but a third, the imidazole 1-oxide (10), is not.Compound (10) was obtained from diacetyl mono-oxime and ammonium carbonate in the absence of cyanide.It is proposed that 4,4-disubstituted 5-imino-oxazolidin-2-ones (18), postulated by Bucherer and Steiner to be intermediates in hydantoin syntheses, rearrange to hydantoins by a base catalysed E1cB mechanism.It is further proposed that (3) is the hypothetical 'dimethylbishydantoin' (35) reported by Bucherer and Lieb in 1934.