Monoalkylphosphinamides: Synthesis and Relative Stability

Amides of Trivalent Phosphorus Acids as Phosphorylating Reagents for Proton-Donating Nucleophiles

“…The study of the rates of alcoholysis of ATPA showed that many reactions of this type are catalytic. This was found for the first time when the rates of phosphorylation of the simplest alcohols by phosph(III)amides thoroughly freed from possible impurities were compared with those by phosph(III)amides obtained by conventional methods and, hence, contaminated by some amine hydrochlorides (AHC). − Later, the discovered catalytic effect has been confirmed by many other researchers. ,,,− …”

“…By now, hydrolysis of phosphorus, ,− phosphonous, and phosphinous , amides has been studied in detail. The results of decomposition of oligomeric and monomeric derivatives were specially compared.…”

“…The results of decomposition of oligomeric and monomeric derivatives were specially compared. It was shown that the first phosphamide bond splits more readily than the other ones. ,,, It is significant that oligoamides can undergo deamidation, after the first hydrolysis event, to give anhydrides (Scheme ) 145 …”

“…[24][25][26] Later, the discovered catalytic effect has been confirmed by many other researchers. 10,17,18,[27][28][29][30][31][32][33][34] The chemical essence of the catalysis had been the object of prolonged debates, the results of which were summarized. 35 Two hypotheses were discussed.…”

“…Phosphorylation of water by ATPA, i.e., hydrolysis of ATPA, is widely employed in synthetic studies for various purposes. The reaction of ATPA with water is appreciably accelerated in the presence of amine hydrohalides 33,665 or azoles. 423 In this respect, the chemical essence of the reaction in question corresponds to that of the above-discussed processes.…”