Reactions of tervalent phosphorus–nitrogen compounds. Part II. Aldehydes and ketones

Abstract

Diethyl N-phenylphosphoramidite reacts with benzaldehyde and with cyclohexanone to give the corresponding a-anilinophosphonate, togetherwith a mixture of diethyl phosphonate and the anil. N-Phenyldiphenylphosphinous amide gives the a-anilinophosphine oxide with benzaldehyde, but the anil with cyclohexanone since the intermediate secondary phosphine oxide decomposes to the biphosphine monoxide in this case. Possible mechanisms for these reactions are briefly discussed. PHOSPHINES are normally unreactive towards aldehydesSimilarly trialkyl phosphites and ketones give a-hydrand ketones except in acidic solution when a-hydroxy-oxyphosphonates in the presence of weak acids by a methyl phosphonium salts are formed according to type of Arbusov r e a ~t i o n . ~ In cold alcoholic solution, the equilibrium :

Facile one-pot synthesis of α-amino phosphonates using lanthanide chloride as catalyst

“…The recovered catalyst was obtained from the aqueous layer after removing water. The spectral and physical data of the known compounds (4a, 4b, 4c, 4k, 4l, 4m [9], 4d, 4e, 4g, 4h, 4i, 4j [5], 4n [17]) were identical with those reported in the literature. The structure of the new compound was determined by 1 …”