33985-75-0Relevant academic research and scientific papers
Solubilities of Phosphoramidic Acid, N-(phenylmethyl)-, Diphenyl Ester in Selected Solvents
Wang, Lijuan,Du, Chaojun,Wang, Xiaojie,Zeng, Hongyan,Yao, Jun,Chen, Baokuan
, p. 1814 - 1822 (2015)
Phosphoramidic acid, N-(phenylmethyl)-, diphenyl ester (PANDE) was synthesized, and its thermostability was measured by thermogravimetric analysis. The melting temperature and the fusion enthalpy of PANDE were evaluated by a differential scanning calorime
Substitution of diarylphosphoryl azides with aliphatic amines catalyzed by simple rare-earth metal salts: Efficient and novel preparation of phosphoryl amides
Peng, Xin-Hua,Bai, Rui,Liu, Shanshan,Li, Zhuo,Jiao, Lin-Yu
, (2021/11/05)
A novel and high efficient protocol was disclosed herein for the rare-earth metal salt-catalyzed substitution of phosphoryl azides with amines. In this homogeneous catalysis system, different diarylphosphoryl azides and aliphatic and aromatic amines were
The Step-Wise Synthesis of Oligomeric Phosphoramidates
Data, Shailja,Leung Wai, Jeffery,Kumar, Saawan,Cameron, Alan J.,Trehet, Manon,Itumoh, Emeka J.,Feld, Joey,S?hnel, Tilo,Leitao, Erin M.
supporting information, p. 5468 - 5477 (2021/09/30)
In this study, the step-wise synthesis to a series of higher phosphoramidates was explored, affording compounds containing N?P?N, symmetric and asymmetric P?N?P and P?N?P?N?P linkages. Salt elimination and lithiation strategies were employed to create the new P?N bonds. It was found that the steric bulk and electronic contribution of the substituents on the P(V) centers were important factors to the success of the reactions. The oligomeric phosphoramidates were characterized by multinuclear NMR and IR spectroscopies as well as ESI mass spectrometry. A selection of the synthesized P?N oligomers were evaluated for their antimicrobial activity against E.coli, S.aureus, C.albicans, and A.fumigatus at varying concentrations. The results suggest their potential use as environmentally friendly fire retardants as the minimal inhibitory concentration (MIC) value for all the compounds was found to be >128 μM, indicating that the compounds do not have any detectable antimicrobial activity.
When phosphoryl azide meets mechanochemistry: Clean, rapid, and efficient synthesis of phosphoryl amides under B(C6F5)3catalysis in a ball mill
Jia, Nan,Jiao, Lin-Yu,Li, Zhuo,Peng, Xin-Hua,Wang, Ze-Lin
, p. 6659 - 6665 (2021/10/25)
We described herein the first example associated with B(C6F5)3-catalyzed preparation of phosphoryl amides under mechanochemical conditions. In this novel system, the combination of energetic reagents with an energetic mechanochemical process enabled the r
Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds
Handoko,Benslimane, Zacharia,Arora, Paramjit S.
supporting information, p. 5811 - 5816 (2020/07/27)
We report a diaryldiselenide catalyst for cross-dehydrogenative nucleophilic functionalization of hydrophosphoryl compounds. The proposed organocatalytic cycle closely resembles the mechanism of the Atherton-Todd reaction, with the catalyst serving as a recyclable analogue of the halogenating agent employed in the named reaction. Phosphorus and selenium NMR studies reveal the existence of a P-Se bond intermediate, and structural analyses indicate a stereospecific reaction.
Transition-metal-free amination phosphoryl azide for the synthesis of phosphoramidates
Li, Qing,Sun, Xiaohua,Yang, Xiaoqin,Wu, Minghu,Sun, Shaofa,Chen, Xiuling
, p. 16040 - 16043 (2019/06/10)
A facile and efficient approach to phosphoramidates was developed via amination of phosphoryl azides. A variety of phosphoramidates were obtained in one step with good to excellent yields under a mild reaction system. The process uses easily available ami
DBN hexafluorophosphate salts as convenient sulfonylating and phosphonylating agents
Jones, Caroline S.,Bull, Steven D.,Williams, Jonathan M. J.
, p. 8452 - 8456 (2016/09/28)
Air-stable N-sulfonyl and N-phosphonyl DBN hexafluorophosphate salts have been synthesised under mild conditions as sulfonylating and phosphonylating agents. These salts are highly efficient in the sulfonylation and phosphonylation of a range of N- and O-nucleophiles to generate sulfonamides, sulfonate esters, phosphoramidates and phosphonate esters in good yields.
Kinetics and mechanism of the benzylaminolysis of O,O-Diphenyl S-Aryl phosphorothioates in dimethyl sulfoxide
Adhikary, Keshab Kumar,Lee, Hai Whang
scheme or table, p. 1625 - 1629 (2011/12/14)
Kinetic studies of the reactions of O,O-diphenyl Z-S-aryl phosphorothioates with X-benzylamines have been carried out in dimethyl sulfoxide at 55.0 °C. The Hammett (log k2 vs ?X) and Broensted [log k2 vs pKa(X)] plots for substituent X variations in the nucleophiles are biphasic concave downwards with a maximum point at X = H, and the unusual positive ρX and negative βX values are obtained for the strongly basic benzylamines. The sign of the cross-interaction constant (ρXZ) is negative for both the strongly and weakly basic nucleophiles. Greater magnitude of ρXZ value is observed with the weakly basic nucleophiles (ρXZ = -2.35) compared to with the strongly basic nucleophiles (ρXZ = -0.03). The deuterium kinetic isotope effects (kH/kD) involving deuterated benzylamines [XC6H4CH2ND2] are primary normal (kH/kD > 1). The proposed mechanism is a concerted SN2 involving a frontside nucleophilic attack with a hydrogen bonded, four-center-type transition state for both the strongly and weakly basic nucleophiles. The unusual positive ρX and negative βX values with the strongly basic benzylamines are rationalized by through-space interaction between the π-clouds of the electron-rich phenyl ring of benzylamine and the phenyl ring of the leaving group thiophenoxide.
Nucleophilic Substitution at the Tetracoordinated Phosphorus Atom. Reactivity of Amines towards Diphenyl Chlorophosphate in Acetonitrile
Solomoichenko,Sadovskii,Savelova,Piskunova,Popov
, p. 1434 - 1441 (2007/10/03)
Tertiary alkylamines, pyridines, and imidazoles catalyze the hydrolysis of diphenylchlorophosphate (acetonitrile, 25°C) by a nucleophilic mechanism with the rate-determining attack of an amine on the substrate. Primary and secondary alkyl and arylamines f
