4707-91-9Relevant academic research and scientific papers
Ultrasound-promoted, rapid and green synthesis of phosphonamide derivatives under catalyst and solvent-free conditions
Bouchareb, Fouzia,Berredjem, Malika,Bouzina, Abdeslem,Guerfi, Meriem
, p. 422 - 430 (2020/12/15)
We report a rapid, efficient, economic, environmentally benign, and easy to scale-up method for the synthesis of phosphonamide derivatives using ultrasound irradiation, under catalyst and solvent-free conditions starting from the corresponding amine and phenyl phosphonic dichloride. The reaction was achieved in excellent isolated yield in a short reaction time at room temperature. The structures of the synthesized compounds are confirmed by elemental analysis as well as by IR and 1H, 13C, 31P NMR spectroscopic data and mass spectrometry.
Preparation and Characterisation of N-(Diphenylphosphinoyl)hydroxylamine, and Conversion into O-Sulphonyl Derivatives that undergo Lossen-like Rearrangement
Harger, Martin J. P.
, p. 2699 - 2704 (2007/10/02)
Having previously shown that diphenylphosphinic chloride (1a) forms O-(diphenylphosphinoyl)hydroxylamine (3a) with hydroxylamine, we have now established that N-(diphenylphosphinoyl)hydroxylamine (2a) can be obtained in good yield by reaction of (1a) with O-trimethylsilylhydroxylamine followed by methanolytic removal of the silyl blocking group.The di-p-tolyl (2b) and bis-p-methoxyphenyl (2c) analogues can be prepared in a similar way.N-(Diphenylphosphinoyl)hydroxylamine is acetylated at the O atom with acetic anhydride, and is sulphonylated at O with methanesulphonyl chloride and toluene-p-sulphonyl chloride.The N-(diphenylphosphinoyl)-O-sulphonylhydroxylamines (8) and (12a) undergo rapid and quantitative Lossen-like rearrangement with methanol-sodium methoxide to give methyl N,P-diphenylphosphonamidate (11).Comparable rearrangement are observed with t-butylamine, aniline-triethylamine, and phenol-triethylamine.
On Diazadiphosphetidines, VI. Synthesis of Diazaphosphetidines, Diazadiphosphetidines, and Thiadiazaphosphetidines
Fluck, Ekkehard,Richter, Horst
, p. 610 - 617 (2007/10/02)
A method of synthesis for the title compounds is reported.The syntheses of 2-(diethylamino)-1,3-dimethyl-1,3,2-diazaphosphetidin-4-one (1), 4-(diethylamino)-1,2,3-triphenyl-1,3,2,4-diazadiphosphetidine 2-oxide (3), and 3-(diethylamino)-2,4-diphenyl-1,2,4,
Three-membered Heterocycles,10. - Phosphonohydrazidic Esters by Alkoxide-induced Rearrangement of N-Chlorophosphonic Diamides
Quast, Helmut,Heuschmann, Manfred,Abdel-Rahman, Mohamed O.
, p. 943 - 966 (2007/10/02)
Phosphoric and phosphonic amides 8 are formed from phosphoric and phosphonic chlorides 6 and primary amines 7 in high yields. 2,5-Dimethyl-2,5-hexanediamine (7e) reacts with phenylphosphonic dichloride (6c) to give the perhydro-1,3,2-diazaphosphepine 8h.The amides 8 are converted almost quantitatively into the N-chlorophosphoric and N-chlorophosphonic amides 9 by means of tert-butyl hypochlorite.The N,N'-di-tert-alkyl-N-chlorophosphonic diamides 9 derived from methyl-, tert-butyl-, or phenylphosphonic acid react with methoxide or tertiary alkoxides to afford the phosphonohydrazidic esters 10-13.The methyl ester 10d is also formed from 1,2,3-tri-tert-butyldiazaphosphiridine 3-oxide (14) and methanol. 1H-, 13C-, and 31P-NMR spectra prove that the sharply melting phosphonohydrazidic esters 10-13 exist in solution as two diastereomers with ratios ranging from 9:1 to 6:4.The hydrazidic methyl ester 10d which was investigated as a representative example exhibits a temperature dependent 1H-NMR spectrum.Due to the presence of the tert-alkyl groups, inversion at the tertiary nitrogen atom is slow on each NMR time scale. The independence of the IR spectrum on the concentration shows that the predominant diastereomer of 10d is stabilized by an intramolecular hydrogen bond.The electron impact induced decomposition of the amides 8, N-chloroamides 9, and phosphonohydrazidic esters 10-13 ultimately produces cations which are derived from monomeric metaphosphoric or metaphosphonic acid. 6 N hydrochloric acid first splits off the P-N-tert-butyl group of the methyl ester 10d to give the intermediate 15 which can be isolated or which undergoes further hydrolysis to tert-butylphosphonic acid (17) and tert-butylhydrazine(19).The tert-butyl ester 11d yields the same final products in hot hydrochloric acid.At low temperatures and short reaction times, however, di-tert-butylhydrazine (18) is formed.
PHOTOLYTIC REARRANGEMENT OF PHOSPHORUS AZIDE : EVIDENCE FOR A TRANSIENT METAPHOSPHONIMIDATE.
Bertrand, Guy,Majoral, Jean-Pierre,Baceiredo, Antoine
, p. 5015 - 5018 (2007/10/02)
Photolysis of the oxide of diphenylphosphine azide gives rise to a transient metaphisphonimidate, a new tricoordinated pentavalent phosphorus compound.Evidence for this species was given by trapping reactions on a variety of substrates.
