Journal of Organic Chemistry p. 4955 - 4963 (1982)
Update date:2022-09-26
Topics:
Cooke, Manning P.
Burman, Diana L.
Charge-directed conjugated addition reactions of the tert-butyl esters of α,β-unsaturated acylphosphoranes 2 have been used to prepare a variety of substituted methyl ketones.Substituted ylides 6 are prepared by alkylating ylide anions 4 generated by the addition of nucleophiles to 2 and are converted under acidic conditions to substituted (acylmethylene)phosphoranes 12 which are hydrolyzed to methyl ketones.The utility of these unsaturated acylphosphoranes as methyl vinyl ketone equivalents in conjugate addition-alkylation reactions is demonstrated in a synthesis of the racemic form of the sex pheromone of the California red scale, 14.
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