ChemInform Abstract: The Horner—Wadsworth—Emmons Reaction of Mixed Phosphonoacetates and Aromatic Aldehydes: Geometrical Selectivity and Computational Investigation.

Abstract

2001alkenes alkenes (benzene compounds) Q 0083 -097The Horner-Wadsworth-Emmons Reaction of Mixed Phosphonoacetates and Aromatic Aldehydes: Geometrical Selectivity and Computational Investigation.-The effect of the electronic nature of the phosphonate substituents on the geometrical selectivity in the Horner-Wadsworth-Emmons reaction is investigated. The reaction with aromatic aldehydes shows gradual change in Z-selectivity according to the electronwithdrawing ability of the phosphonoacetate substituents. There is a good correlation between the observed selectivities and 31 P chemical shifts of the phosphonoacetates. In addition, the effect of reaction conditions (base, additive) on the ratio of Z-and E-cinnamates is reported. -(MOTOYOSHIYA, JIRO;