Enol Phosphates from the Action of Monomeric Metaphosphate Ion on Ketones

Article abstract of DOI:10.1021/ja00347a051

Prior research from this laboratory had demonstrated that monomeric metaphosphate ion, generated by fragmentation from β-bromophosphonate dianions, reacts with acetophenone in the presence of excess base to give a modest yield of 1-phenylvinyl phosphate.This paper expands on that finding; it presents studies of the effects of concentration of reagents, of solvents, and of variation in amine structure (i.e., of the base) on the reaction.These studies lead to experimental conditions where the yield of the enol phosphate of acetophenone, based on the β-bromophosphonic acid used, exceeds 80percent.Several other ketones can be similarly converted to their enol phosphates, although in inferior yield.