126180-52-7

Upstream product

• 71457-20-0 P-methyl-P-phenyl-P-(ortho-tolyl)phosphine oxide 
• 6389-79-3 methyl methylphenylphosphinate 
• 932-31-0 ortho-tolylmagnesium bromide 
• 41924-67-8 (phenyl)(ortho-toluene)chlorophosphane 
• 75-16-1 methylmagnesium bromide 
• 71779-60-7 (R_P)-methylphenyl(o-methylphenyl)phosphine 
• 5761-97-7 methyl(phenyl)phosphinic chloride 
• 20685-01-2 Methylphenylamino-phenylchlorphosphin 
• 644-97-3 Dichlorophenylphosphine 
• 2946-61-4 phenylphosphonous acid dimethyl ester 
• 506-82-1 dimethylcadmium 
• 917-54-4 methyllithium 
• 202977-10-4 C₂₀H₂₀NP 
• 17310-32-6 (CH₃C₆H₄)2Cd 

Downstream Products

• 71457-20-0 P-methyl-P-phenyl-P-(ortho-tolyl)phosphine oxide 
• 71779-60-7 (R_P)-methylphenyl(o-methylphenyl)phosphine 
• 181480-95-5 methylphenyl(o-methylphenyl)phosphine borane 

Relevant academic research and scientific papers

Turning regioselectivity into stereoselectivity: Efficient dual resolution of P-stereogenic phosphine oxides through bifurcation of the reaction pathway of a common intermediate

Synthetic routes that provide facile access to either enantiomeric form of a target compound are particularly valuable. The crystallization-free dual resolution of phosphine oxides that gives highly enantioenriched materials (up to 94 % ee) in excellent y

Formation of unexpected heterocyclic products from pyrolysis of thiocarbonyl stabilised phosphonium ylides

Chiral phthalimido thioxo-stabilised phosphonium ylides, prepared starting from (S)-alanine and (S)-phenylalanine, undergo intramolecular Wittig reaction upon pyrolysis leading to the previously unknown pyrrolo[2,1-a]isoindol-5-one-2- thiones, rather than

Catalyzing pyramidal inversion: Configurational lability of P-stereogenic phosphines via single electron oxidation

We report that pyramidal inversion of trivalent phosphines may be catalyzed by single electron oxidation. Specifically, a series of P-stereogenic (aryl)methylphenyl phosphines are shown to undergo rapid racemization at ambient temperature when exposed to catalytic quantities of a single electron oxidant in solution. Under these conditions, transient phosphoniumyl radical cations (R3P?+) are formed, and computational models indicate that the pyramidal inversion barriers for these open-shell intermediates are on the order of ～5 kcal/mol. The observed 1020-fold rate enhancement over uncatalyzed pyramidal inversion opens new opportunities for the dynamic stereochemistry of phosphines and may hold additional implications for the configurational stability of P-stereogenic phosphine ligands on high-valent oxidizing transition metals.

A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions

A mild method for the facile removal of phosphine oxide from the crude products of Wittig and Appel reactions is described. Work-up with oxalyl chloride to generate insoluble chlorophosphonium salt (CPS) yields phosphorus-free products for a wide variety of these reactions. The CPS product can be further converted into phosphine.

P-stereogenic phosphorus compounds: Effect of aryl substituents on the oxidation of arylmethylphenylphosphanes under asymmetric appel conditions

The effects of aryl ring substitution on the dynamic resolution of aryl(methyl)phenylphosphanes under asymmetric Appel reaction conditions have been studied. As expected, substitution at the ortho position strongly affects the degree ofstereoselection tha

Synthesis of P-stereogenic phosphorus compounds. Asymmetric oxidation of phosphines under appel conditions

Racemic phosphines are converted into enantioenriched phosphine oxides via a synthetically simple, but theoretically interesting, oxidation procedure in good enantiomeric excess (up to 80%) and excellent yields (>95%). These phosphine oxides can be oxidatively coupled to provide easy access to enantiopure DiPAMPO analogues. Particularly attractive aspects of this procedure are the operational simplicity and the low cost required to synthesize these high value compounds. Copyright

A novel synthesis of unsymmetrical tertiary phosphines: Selective nucleophilic substitution on phosphorus(III)

A new synthesis of unsymmetrical tertiary phosphines has been developed employing selective, sequential alkylation of chloroaminophospnines by Grignard and organolithium reagents.

Thermal Stability of Phosphinoacetic Acids

Phosphinoacetic acids decarboxylate smoothly in toluene solution at 99 deg C and the corresponding alkylphosphine is formed in quantitative yields.Electron-withdrawing substituents at the α position of the carboxylic acid lead to a large increase in the reaction rate.In contrast, electron-withdrawing substituents at the phosphorus atom lead to a small decrease in the rate.We have concluded from the substituent effects, solvent effects, and the influence of bases and acids that both the lone pair of the phosphorus atom and the carboxylate hydrogen atom play a crucial role in the reaction.A mechanism is proposed that proceeds via an ylide.Sodium phosphinocarboxylates do not decarboxylate in an aqueous solution at 95 deg C.Instead a carbon-phosphorus bond cleavage occurs probably by an intramolecular nucleophilic substitution.

FACILE REDUCTION OF ORGANIC HALIDES AND PHOSPHINE OXIDES WITH LiAlH4-CeCl3

A new reagent system, LiAlH4-CeCl3, exhibits powerful and characteristic reducing ability.Organic halides including fluorine compounds are smoothly dehalogenated with this reagent.Phosphine oxides are also reduced to phosphines in excellent yields.

SYNTHESE DIRECTE DE PHOSPHINES TERTIARIES RACEMIQUES ET DE CHLOROPHOSPHINES DISSYMETRIQUES

Racemic tertiary phosphines are obtained from dichlorophenylphosphine by a "one pot" synthesis in two steps: (1) condensation of one equivalent of an organocadmium, and (2) substitution of the second chlorine by another organometallic compound.The phosphines liberated from the resulting complexes can be stabilised by direct complexation with cuprous salts.The monochlorophosphines can be isolated in the first stage when their cadmium complexes are submitted to ligand exchange with pyridine.