Novel beta-oximinoalkylphosphonic acid ester derivatives and method of preparation.

摘要

Novel β-oximinoalkylphosphonic acid ester derivatives of general formula 8 are prepared from the corresponding α-halo oxime A:
wherein R' is a substituent selected from the group consisting of H and C₁-C₂₀ alkyl, cycloalkyl and aryl substituents;
R² is a substituent selected from the group consisting of H and C, to C₂₀ linear alkyl and aryl substituents;R³ is a substituent selected from the group consisting of H and C, to C₂₀ alkyl, cycloalkyl, 1-alkoxy alkyl, aryl, acyl, N-substituted carbamoyl, N,N-disubstituted carbamoyl and nitrogen-, oxygen-, sulfur-, and phosphorus-containing heterocyclic substituents;R⁴ is an alkyl substituent of C, to C₂₀ andX is a substituent selected from the group consisting of Cl, Br, I.

In a specific reaction, the a-halo oxime derivative is dissolved in an excess of trialkyl phosphite, greater than 3 molar equivalents is preferred. The preference for the a-halogen atom follows the order I>>Br>>Cl which parallels their rate of reaction with trialkyl phosphite. The acceptable temperature range includes ambient conditions. The reaction can be run in various solvents including tetrahydrofuran, toluene and acetonitrile.