Journal of Organic Chemistry p. 948 - 955 (1983)
Update date:2022-08-04
Topics:
Fischetti, William
Mak, K. Tim
Stakem, F. Gregory
Kim, Jin-Il
Rheingold, Arnold L.
Heck, Richard F.
Conjugated trienes have been prepared by the palladium-catalyzed reaction of vinylic bromides with 2,4-pentadienoic acid and its 3-methyl derivative, in the presence of triethylamine.Methyl (E)-3-bromo-2-methylpropenoate also forms conjugated trienes and in some instances also tetraenes when it is reacted with 1,3-dienes under similar conditions.Some loss of stereochemistry in the starting vinylic bromide or, more often, in the diene may occur in the rections presumably because equilibrating ?-allylic intermediates are involved.1,3,5-Hexatriene and 2 equiv of methyl (E)-3-bromo-3-methylpropenoate form orange-red dimethyl (E,E,E,E,E)-2,11-dimethyl-2,4,6,8,10-dodecapentaenedioate in modest yield.
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