Synthesis and reactions of (E)- and (Z)-1,3-dibromo-2-methoxypropene
(Z)-1,3-Dibromo-2-methoxypropene is prepared in 90% yield by dehydrohalogenation of 1,2,3-tribromo-2-methoxypropane with diisopropylamine in dichloromethane. The E-isomer can be obtained as the only product in almost quantitative yield by UV irradiation of the Z-isomer. Nucleophilic displacement reactions of the allylic bromide and palladium-catalyzed coupling reactions of the vinylic bromide in (E)- and (Z)-1,3-dibromo-2-methoxypropene have been studied.
Edvardsen
KR
Department of Chemistry, University of Hawaii at Manoa, 2545 The Mall, Honolulu, Hawaii 96822, USA.
Benneche
T
Tius
MA