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Unexpected Non-Stability of Aminophosphonates: Limitation of Their Synthesis Using Diphenylmethylamine Procedure

Zoń J., Miziak P., Rychlewski T., Gancarz R.

Polish Journal of Chemistry

2007

Vol. 81, nr 11

2023-2030

New diethyl 1-diphenylmethylaminoalkylphosphonates from aldehydes, ketones, diphenyl methylamine and diethyl phosphite were obtained. Their stability in acidic media as determined by 31P NMR spectroscopy strongly depends on the basicity of the nitrogen atom. The bulky N-substituent can drastically decrease the stability of the ester during acidic hydrolysis leading to decomposition products in the retro Kabachnik-Fields like reaction.