The protonation equilibria in aminophosphonates: protonation on nitrogen vs phosphoryl oxygen has been calculated. The calculated energy differences explain satisfactory experimentally observed tendency toward nonstability of aminophoshonates in acidic media.
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.
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