37097-43-1Relevant articles and documents
Phosphoramidate synthesis via copper-catalysed aerobic oxidative coupling of amines and H-phosphonates
Fraser, Jamie,Wilson, Laura J.,Blundell, Rebecca K.,Hayes, Christopher J.
supporting information, p. 8919 - 8921 (2013/09/24)
The copper-catalysed oxidative coupling of amines and H-phosphonates to produce phosphoramidates has been achieved using CuI as the catalyst and O 2 (present in air) as the sole oxidant.
Nucleophilic substitution reactions of diethyl 4-nitrophenyl phosphate triester: Kinetics and mechanism
Castro, Enrique A.,Ugarte, Daniela,Rojas, M. Fernanda,Pavez, Paulina,Santos, Jose G.
supporting information; experimental part, p. 708 - 714 (2012/08/08)
The reactions of diethyl 4-nitrophenyl phosphate (1) with a series of nucleophiles: phenoxides, secondary alicyclic (SA) amines, and pyridines are subjected to a kinetic study. Under excess of nucleophile, all the reactions obey pseudo-first-order kinetics and are first order in the nucleophile. The nucleophilic rate constants (kN) obtained are pH independent for all the reactions studied. The Bronsted-type plot (log kN vs. pKa nucleophile) obtained for the phenolysis is linear with slope β=0.21; no break was found at pKa 7.5, consistent with a concerted mechanism. The Bronsted-type plots for the SA aminolysis and pyridinolysis are linear with slopes β=0.39 and 0.43, respectively, also suggesting concerted processes. The concerted mechanisms for the latter reactions are proposed on the basis of the lack of break in the Bronsted-type plots and the instability of the hypothetical pentacoordinate intermediates formed in these reactions.
SOLVOLYSIS OF DIPHENYL AMIDOPHOSPHATES IN AQUEOUS ALCOHOLIC MEDIA
Kasparek, Frantisek,Mollin, Jiri
, p. 386 - 396 (2007/10/02)
Influence of substituent on the reaction rate of the alkali-catalyzed solvolysis of the studied compounds set has been followed.The activation entropy has also been determined.The reaction products have been identified, and their concentration ratio has been determined.The reaction selectivity is mostly influenced by sterical effects in the substrate molecule.The results obtained agree with the SN2 mechanism.
REACTION OF SULFENAMIDES WITH DI-ALKYL AND TRIALKYL PHOSPHITES. AN EFFICIENT SYNTHESIS OF PHOSPHORAMIDATES BY UNUSUAL SUBSTITUTION AT S-N BOND IN (2-BENZOTHIAZOLYL)SULFENAMIDES
Torii, Sigeru,Sayo, Noboru,Tanaka, Hideo
, p. 695 - 698 (2007/10/02)
Regioselective attack of the trivalent phosphorus atom of dialkyl and trialkyl phosphites on either nitrogen or sulfur atom of sulfenamides has been found.The reaction of phenylsulfenamides with dialkyl phosphites yielded phosphorothiolates, whereas the treatment of (2-benzothiazolyl)sulfenamides with dialkyl and trialkyl phosphites gave phosphoramidates in excellent yields.