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

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

Source and publish data:

Tetrahedron Letters p. 6269 - 6272 (1990)

Update date:2022-08-04

Topics:

Authors:

Graham, Samuel L.

Scholz, Thomas H.

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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.

Full text of DOI:10.1016/S0040-4039(00)97039-4

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