At 180-190°C and in the presence of a weak base (usually K2CO3), ketoximes bearing an a-methylene react with DMC to yield N-methyl oxazolinones (Scheme 4.14).34 This reaction is general for both linear and cyclic oximes, and exemplifies a selective methoxycarbonylation reaction at a high temperature. In fact, the first step is the BAc2 attack of the oxygen atom on the DMC carbonyl. Then, the reaction proceeds through an N-methylation and a final [3,3]-sigmatropic rearrangement, as shown in Scheme 4.15.

k2co3 R'vn

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