Journal
TETRAHEDRON
Volume 59, Issue 8, Pages 1181-1189Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(03)00041-3
Keywords
Baylis-Hillman reaction; Lewis base; methyl vinyl ketone (MVK); ethyl vinyl ketone (EVK); DABCO; conjugated addition; DMAP
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In the Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone (MVK), we found that, besides the normal Baylis-Ellman adduct 1, the diadduct 2 can also be formed at the same time and the yield of 2 can reach to 55% if increasing the amount of methyl vinyl ketone. But for ethyl vinyl ketone (EVK), methyl acrylate or acrylonitrile, only the normal Baylis-Hillman adduct 4, 7 or 8 was obtained, respectively. The substituent's effects and Lewis base effects were also examined and a plausible reaction mechanism was proposed for the formation of 2. (C) 2003 Elsevier Science Ltd. All rights reserved.
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