Canadian journal of chemistry

The reactions of simple dimethylallylamines with dimethyl acetylenedicarboxylate. Formation of 1-dimethylamino-2-allylmaleates via formal allyl transfer

AL Schwan, J Warkentin

Index: Schwan, Adrian L.; Warkentin, John Canadian Journal of Chemistry, 1988 , vol. 66, p. 1686 - 1694

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Citation Number: 22

Abstract

Tertiary amines bearing two methyl groups and an allylic substituent (X) react with dimethyl acetylenedicarboxylate (DMAD) to afford the corresponding 1-dimethylamino-2-X'maleates, in which X'is the allylic isomer of X. The mechanism postulated involves reversible formation of a zwitterion by attack of the amine at an sp-carbon of DMAD. The zwitterion then undergoes intramolecular allyl transfer, through a 6-membered transition state. Evidence ...