Journal of Organic Chemistry p. 5765 - 5770 (1993)
Update date:2022-07-30
Topics:
Marques, C. A.
Selva, M.
Tundo, P.
Montanari, F.
The reaction of ketone oximes with dimethyl carbonate (DMC) carried out in an autoclave at 180-190 deg C and in the presence of K2CO3 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 48percent.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.
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