Wittig reagents and method for preparing .alpha.,.beta.-unsaturated phosphonates

Abstract

Wittig-type reagents and methods of preparation and use thereof for preparing .alpha.,.beta.-unsaturated phosphonate esters from aldehydes and ketones are disclosed. The Wittig-type reagents have the following formulae: ##STR1## wherein X represents triflate, halide, BF.sub.4, SbF.sub.6, or ClO.sub.4 ; R.sub.1 represents alkyl, aryl or arylalkyl; and R.sub.2 represents alkyl, aryl or arylalkyl, provided that R.sub.1 and R.sub.2 not represent phenyl at the same time. The Wittig reagent diethyl phosphono-methylidenetriphenylphosphorane (1b) has been successfully synthesized for the first time via its phosphonium triflate salt (4a), by treating diethyl phosphonomethyltriflate with triphenylphosphine according to the disclosed method. The procedure has been applied to the synthesis of other new Wittig-type reagents such as phosphoranes and phosphonium salts. The new Wittig reagents thus synthesized were treated with various aldehydes and an activated ketone, affording the corresponding .alpha.,.beta.-unsaturated phosphonates, saturated phosphonates or phosphoric acids. Triphenylphosphorane 1b and triphenylphosphonium 4a led to both cis and trans isomers with the latter being predominant, while trans isomers were almost exclusively formed when tributyl reagents (1c and 4d) were used.

Dependencies are inferred from the claim text.