Reactions of aldoketeniminophosphonates with CH-acids

Abstract

Aiming to obtain new polyfunctional organophosphorus compounds, we studied the reactions of aldoketeniminophosphonates with different CH-acids. The reactions were shown to proceed efficiently in anhydrous acetonitrile medium in the presence of the catalytic amounts of potassium carbonate to form the products of the addition of CH-acids to a multiple carbon-carbon bond followed by the prototropic isomerization to the corresponding γ-substituted β-functional alkylaminoethenephosphonates. The reaction of aldoketeniminophosphonates with CH-acids is found to depend significantly on the strength and nature of the acid. The formation of the carbon-carbon bond is possible mainly in the case of the CH-acids whose pK _a values lie within 10–14.