A New Mode of Reactivity of N-Methoxy-N-methylamides with Strongly Basic Reagents

Article abstract of DOI:10.1016/S0040-4039(00)97039-4

In applying N-methoxy-N-methylamides as acylating agents for carbanions, an unusual mode of reactivity was discovered.In particular, competitive transfer of a hydroxymethyl group was observed.The mechanism of this reaction is described, and involves a base induced E2 elimination of the N-methoxy-N-methylamide generating formaldehyde and the corresponding N-methylamide anion.