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Reaction of 1,3,4-tribromo-2-alkanones, efficiently prepared by direct bromination of the parent enone, with methanolic sodium methoxide gives methyl ( Z )-2,4-pentadienoates with high ( Z ) selectivity about the α,β-double bond.

The title compound is prepared efficiently and stereoselectively by sodium methoxide induced Favorskii rearrangement and elimination of HBr from 4-methyl-1,3,4-tribromo-2-pentanone which is formed by direct bromination of mesityl oxide. The method provides mole quantities of the title compound.

The title compound is prepared efficiently and stereoselectively by sodium methoxide induced Favorskii rearrangement and elimination of HBr from 4-methyl-1,3,4-tribromo-2-pentanone which is formed by direct bromination of mesityl oxide. The method provides mole quantities of the title compound.

1,3-Dibromo-1-phenylacetones, readily prepared by direct bromination of the parent phenylacetone, react with methanolic sodium methoxide to yield stereoselectively methyl ( Z ) cinnamates in good yield.