Stereochemistry of the reaction of 2,3-dibromo-ketones with phenoxide ion in DMF

ABSTRACT

The reaction of a series of erythro-2,3-dibromo-1,3-arylpropanones l[a-K] with sodium phenoxide in dimethyl-formamide [DMF] was investigated. 3-Phenoxy-l,3-diaryl-propenones 2[a-k] were obtained as a mixture of E- and Z/isomer and their configuration were established by spectral studies. A stepwise mechanism is postulated for this reaction proceeds via an intermediate carbanions