C. Marques, M. Selva, P. Tundo
Oct 1, 1993
Citations
0
Influential Citations
31
Citations
Journal
Journal of Organic Chemistry
Abstract
The reaction of ketone oximes with dimethyl carbonate (DMC) carried out in an autoclave at 180-190 o C and in the presence of K 2 CO 3 yields 3-methyl-4,5-disubstituted-4-oxazolin-2-ones. The reaction can be applied to both aliphatic and aromatic ketone oximes, provided that a methylene group be present near the C=N bond. Nonoptimized yields range from 22 to 48%. The reaction seems to be a [3,3] sigmatropic rearrangement where DMC plays a key role in causing the initial N-methylation of the oximes