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Upstream product

• 64-17-5 ethanol 
• 58816-54-9 1-(methoxy-phenyl-phosphinoyl)-5-phenyl-1H-pyrazole-3-carboxylic acid methyl ester 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 1638-86-4 diethyl phenylphosphonite 
• 4546-19-4 ethyl hydrogen phenylphosphonate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1571-33-1 phenylphosphonate 
• 56252-44-9 N-(1-adamantyl)phenylphosphonochloramidate 
• 182175-26-4 N-(1-adamantyl)phenylphosphonamidic acid 
• 172487-18-2 ethyl Phenylphosphinate 
• 1779-48-2 phenylphosphinic acid 
• 88066-01-7 2-N-<(R)-thiophosphoryl>glucosamine 

Relevant academic research and scientific papers

Direct aerobic oxidative esterification and arylation of P(O)-OH compounds with alcohols and diaryliodonium triflates

Copper-catalyzed aerobic oxidative esterification of P(O)-OH compounds is achieved using alcohols as efficient esterification reagents, giving the expected products with good to moderate yields. Furthermore, it is shown that the arylation of P(O)-OH compounds proceeds efficiently to produce the corresponding products via the treatment of diaryliodonium triflates under mild reaction conditions. It is a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. The protocol is convenient for practical application. A plausible mechanism has been proposed for the reaction.

Synthesis of the mixed alkyl esters of phenylphosphonic acid by two variations of the Atherton-Todd protocol

Phenylphosphonates with mixed alkyl groups were synthesized from ethyl phenyl-H-phosphinate by twomodified Atherton-Todd methods. Using aqueous sodium hydroxide under phase transfer catalytic conditions, the alkyl ethyl phosphonates were obtained in onlym

Stereochemical inversion of phosphonothioate methanolysis by La(III) and Zn(II): Mechanistic implications for the degradation of organophosphate neurotoxins

The utility of phosphonothioate methanolysis to degrade organophosphate neurotoxins has prompted the stereochemical investigation of this useful transformation. The methanolysis of enantiomerically pure O,S-diethyl phenylphosphonothioate (5) was studied b

Synthesis of alkyl- and arylphosphonic acid monoesters by direct esterification of dibasic phosphonic acids in the presence of an arsonic acid catalyst

Partial hydrolysis of a diester, hydrolysis of the monochloro monoester, or alcoholysis of a phosphonic acid anhydride generally is used to prepare monoesters of alkyl- and arylphosphonic acids. Limited cases have been reported for the esterification of a dibasic phosphonic acid to yield the monoester, and none of these methods are as simple as the analogous method for preparing carboxylic acid esters, in which the carboxylic acid is esterified with an alcohol in the presence of an acid catalyst. Described is a method for preparing monoesters of alkyl- and arylphosphonic acids by direct esterification with an alcohol in the presence of a catalytic amount of phenylarsonic acid. The water formed during the reaction is removed azeotropically. For example, methylphosphonic acid was esterified in good yield to give its isopropyl, butyl, cyclohexyl, bornyl, and octadecyl monoesters. Similarly prepared are the ethyl, butyl, hexyl, and 2-(ethylthio)ethyl monoesters of phenylphosphonic acid, as well as 2-isopropoxyethyl hydrogen ethylphosphonate and 2-methoxyethyl hydrogen benzylphosphonate.

Dichotomy in the reactivity of trivalent phosphorus compounds Z3P (Z = Ph, nBu, OR) observed in the photoreaction with a ruthenium complex

Solutions of tris(2,2′-bipyridyl)ruthenium(II) dichloride (Ru2+) and various types of trivalent phosphorus compounds Z3P (Z = Ph, nBu, OR; 1) in methanol have been photolyzed with visible light at 20 °C under an argon atmosphere, resulting in the oxidation of I to the corresponding pentavalent oxo compounds Z3P=O and ligand exchange of Ru2+ with 1. The former process takes place via single-electron transfer (SET) from 1 to Ru2+ in the photoexcited state, Ru2+*, which gene-rates the radical cation intermediate Z3P*+ from 1. The latter results from nucleophilic attack of 1 upon Ru2+*. The results show that 1 can act either as an electron donor or as a nucleo-phile toward Ru2+*. The rate constants for both processes are estimated. An excellent linear correlation is found between the logarithm of the SET rate and the oxidation potential for both the aromatic and aliphatic trivalent phosphorus compounds examined here; the slope of the plot is much less negative than expected on the basis of Rehm-Weller theory. Such behavior in the SET rates is interpreted by comparison with SET quenching by amines. On the other hand, a dualparameter correlation analysis shows that the ligand exchange is regulated by both steric and electronic factors in 1. WILEY-VCH Verlag GmbH, 1997.

Fragmentation of a phenylphosphonamidic acid as a new technique for the generation of phenyl dioxophosphorane

N-(1-Adamantyl) phenylphosphonamidic acid (3), an easily prepared solid, on heating in toluene or 1,2-dichloroethane gave the crystalline adamantylamine salt of the anhydride PhP(O)(NHAd)-O-PPh(O)(OH). The mechanism is proposed to involve first the fragmentation of 3 to form phenyl dioxophosphorane, PhPO2, which then acts as a phosphorylating agent to unreacted 3. This mechanism was supported by the observation of first-order kinetics for the consumption of 3. When the phosphonamidic acid was fragmented in the presence of an alcohol, the intermediate PhPO2 was trapped as the monoalkyl phenylphosphonate. The OH groups on the surface of silica gel were also phosphonylated by PhPO2. The acidic OH group of a phosphoric acid monoester (thymyl phosphate) was phosphonylated to give Thy-O-P(O)(OH)-O-PPh(O)(OH). It is concluded from this study that N-(1-adamantyl) phenylphosphonamidic acid is a useful precursor of phenyl dioxophosphorane, which can perform valuable phosphonylation operations.

Kinetic Facial Selectivity in Nucleophilic Displacements at Tetracoordinate Phosphorus: Kinetics and Stereochemistry in the Reaction of Sodium Ethoxide with O,S-Dimethyl Phenylphosphonothioate

The reaction of ethoxide ion with O,S-dimethyl phenylphosphonothioate (1a) proceeds with competitive displacements of the methylthio and methoxy ligands.Each displacement occurs with complete inversion of configuration.The two products, ethyl methyl pheny

Chromatographic Resolution of Racemic Compounds Containing Phosphorus or Sulfur Atom as Chiral Center

Racemic compounds containing a phosphorus or a sulfur atom as a chiral center were resolved by high-performance liquid chromatography on optically active (+)-poly(triphenylmethyl methacrylate).The resolved compounds include insecticides such as O-ethyl O-(4-nitrophenyl)phenylphosphonothionate (EPN), O-(4-cyanophenyl)-O-ethyl phenylphosphonothionate (cyanofenfos), and 2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-sulfide (salithion).

Use of Carbohydrate Derivatives for Studies of Phosphorus Stereochemistry. Part 8. Preparation and Some Reactions of 1,3,2-Oxazaphospholidine-2-ones and -2-thiones derived from 2-Deoxy-3,4,6-tri-O-methyl-2-methylamino-D-glucopyranose

The four cyclic phosphorus esters from the reaction of MePSCl2 with 2-deoxy-3,4,6-tri-O-methyl-2-methylamino-D-glucopyranose (1) have been separated with difficulty, and structures assigned.Ring-opening of the isomers and subsequent detachment of the chir

Stereochemistry and Reactions of Aziridinylphosphinothionates Derived from Amino Acids

Aziridinylphosphinothionates were prepared from optically active ethyl hydrogen phenylphosphonothionates and 1-bromo-2-alkanamines derived from leucine or valine.The aziridine ring was opened by the action of some nucleophiles.Refluxing the aziridinylphosphinethionates in acetone with sodium iodide caused hydrolysis accompanied by the rearrangement of the sulfur atom to give β-mercaptoethylphosphonamidates.The reaction mechanism was discussed eith stereochemical considerations.The insecticidal activity of the products was also examined.