The reactions of simple dimethylallylamines with dimethyl acetylenedicarboxylate. Formation of 1-dimethylamino-2-allylmaleates via formal allyl transfer
AL Schwan, J Warkentin
文献索引：Schwan, Adrian L.; Warkentin, John Canadian Journal of Chemistry, 1988 , vol. 66, p. 1686 - 1694
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 ...
