ORGANOPHOSPHORUS CHEMISTRY 10. THE BEHAVIOUR OF β-AROYLACRYLIC ACIDS TOWARD NUCLEOPHILIC PHOSPHORUS COMPOUNDS

Abstract

The reaction of alkyl phosphites and thiolphosphoric acids with β-aroylacrylic acids 1a,b has been investigated. Dialkyl phosphites (DAP) attacked 1 at the β-carbon atom with respect to the aroyl-carbonyl function, to give phosphonate 1:1 adducts assigned structure 2A. Thiolphosphoric acids (7) attacked 1 at the same centre to give adducts 8. On the other hand, trialkyl phosphites (TAP) converted 1 into the respective esters 5, almost exclusively. Structures of the new products were assigned according to consistent analytical and spectroscopic measurements.

Key Words:

• β-Aroylacrylic acids
• alkylation
• phosphorylation
• thiophosphorylation.