34868-25-2

Upstream product

• 74-83-9 methyl bromide 
• 7650-90-0 dibenzylphenylphosphane 
• 33838-34-5 methylbenzylphenylphosphine oxide 
• 63832-87-1 iodure de methylbenzyldiphenylphosphonium 
• 64030-44-0 (2S)-2-(anilinomethyl)pyrrolidine 
• 506-82-1 dimethylcadmium 
• 644-97-3 Dichlorophenylphosphine 
• 17051-04-6 dibenzyl cadmium 
• 100-39-0 benzyl bromide 
• 6372-48-1 methylphenylphosphine 
• 721-74-4 R(+)-benzyl methyl phenyl phosphine oxide 
• 917-54-4 methyllithium 
• 29949-68-6 benzyl-phenylchlorophosphine 
• 184776-08-7 (Sp)-1,2:3,5-diisopropylidene-α-D-glucofuranosyl benzylphenylphosphinite 

Downstream Products

• 24153-81-9 Methyl-phenyl-benzyl-benzhydryl-phosphonium 
• 98170-69-5 Tetramethylen-bis- 
• 24153-84-2 Allyl-benzyl-methyl-phenyl-phosphonium-bromid 
• 72144-86-6 Dimethyl-phenyl-benzyl-phosphonium 
• 33838-34-5 methylbenzylphenylphosphine oxide 
• 117917-33-6 {Ru3(CO)9(μ3-η2-C2tBu)}(μ4-Hg){Ru3(μ3-η2-C2tBu)(P(CH3)(C6H5CH2)(C6H5))} 

Relevant academic research and scientific papers

Method for enantioselective synthesis of phosphorus-stereogenic phosphines

The present invention relates to a process for preparing an enantioenriched phosphorus-stereogenic, tertiary phosphine. Secondary phosphines are contacted with an alkyl halide and base in the presence of a chiral metal catalyst thereby producing the enantioenriched phosphorus-stereogenic, tertiary phosphine for subsequent use in homogeneous catalysis reactions.

METHOD FOR ENANTIOSELECTIVE SYNTHESIS OF PHOSPHORUS-STEREOGENIC PHOSPHINES

The present invention relates to a process for preparing an enantioenriched phosphorus-stereogenic, tertiary phosphine. Secondary phosphines are contacted with an alkyl halide and base in the presence of a chiral metal catalyst thereby producing the enantioenriched phosphorus-stereogenic, tertiary phosphine for subsequent use in homogeneous catalysis reactions.

Asymmetric induction in the reaction of nonsymmetrical phosphinic and phosphinous acid clorides with derivatives of D-glucofuranose

Reaction of nonsymmetrically substituted chlorophosphines (1-3) with (-)-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose (1) or (-)-1,2:5,6-di-O-cyclohexylidene-α-D-glucofuranose (5) proceeds with high stereoselectivity to give stereochemically pure phosphinic acid esters (6-8), which are starting compounds for the preparation of chiral organophosphorus compounds. Reaction of benzyl-phenylphosphinous acid chloride with (1) leads to optically pure phosphinous acid ester (9). The stereochemistry of the reaction is studied in dependence on the nature of the base, solvent, temperature and excess of chlorophosphine.

Simple route to chiral organophosphorus compounds

Reaction of chlorides of nonsymmetrically substituted phosphinic and phosphinous acid with (-)-1,2,3,5-disubstituted-α-D-glucofuranose proceeds with very high stereoselectivity to give stereochemically pure phosphinic and phosphinous acid esters, which are starting reagents for preparation of chiral organophosphorus compounds. Stereoselectivity of the reaction depends on the nature of bases, solvent, temperatures and excess of chlorophosphine.

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.

THE PREPARATION OF OPTICALLY ACTIVE PHOSPHINES BY ASYMMETRIC REDUCTION OF RACEMIC PHOSPHINE OXIDES

The reduction of (R,S)-1-phenyl-3-methyl-2-phospholene 1-oxide (3) with lithium aluminium hydride has been studied to explain some of the anomalies reported for the reduction of (3) with optically active alanes.Reductions of acyclic racemic chiral phosphines oxides using optically active alanes and lithium aluminium hydride doped with (S)-2-(anilinomethyl)-pyrrolidine is reported, both giving optically active phosphines with low enantiomeric excesses.

PHOSPHORORGANISCHE VERBINDUNGEN 104. TERTIAERE PHOSPHINE BZW. ARSINE DURCH REDUKTIVE SPALTUNG QUARTAERER PHOSPHONIUM- UND ARSONIUMSALZE MIT ALKALIAMALGAMEN

The reductive cleavage of achiral and optical active quaternary phosphonium and arsonium salts with alkali metal amalgams forming tertiary phosphines and tertiary arsines succeeds in high yields at room-temperature with retention of configuration.In the r

Optically Active Phosphines. Facile Preparation of the Optically Active n-Propylmethylbenzyl- and Methylphenylbenzylphosphine Oxides as Precursors to the Corresponding Tertiary Phosphines

The optically active phosphine oxides MePhP(O)CH2Ph (6) and n-PrMeP(O)CH2Ph (9) are readily prepared by a new route from the easily available, essentially optically pure, O-isopropyl S-alkyl methylphosphonothioates 4 and 7.Two successive Grignard reactions give 6 in 52-55percent and 9 in 18-24percent overall chemical yields.Reductions of 6 and 9 with PhSiH3 afford the corresponding optically active phosphines MePhCH2Ph (1) and n-PrMePCH2Ph (2) of optical purities (45-70percent and 53-57percent, respectively) which are quite suitable for studies of the stereochemistries of reactions occurring at phosphorus.The relative ease of the procedure and the fact that both enantiomers are equally readily available especially recommend this route for the preperation of 1.Moreover, no other experimentally detailed, published method for the preparation of an optically active trialkylphosphine such as 2 in reasonably high optical purity is available.The route to phosphine 1 depends on the use of potentially tridentate ligand (SCH2CH2OCH2CH2OCH2CH3) on phosphorus which activates 4 toward reaction with PhMgBr and also allows CH3CH2OCH2CH2OCH2CH2 to be selectively displaced.Quite surprisingly, this displacement occurs with inversion of configuration at phosphorus by contrast to the retentive stereochemistry normally observed on reaction of O-alkyl S-alkyl methylphosphonothioates with Grignards.Evidence is also presented for the potential generality of this method for the preparation of optically active dialkylphenyl- and trialkylphosphines.

Preparation and (31)P nuclear magnetic resonance studies of chiral phosphines

The reaction of Li metal with alkyldiphenylphosphines generates the alkylphenylphosphide anions, which can undergo subsequent reactions with alkyl halides to give chiral phosphines (RR'R''P).The (31)P nmr chemical shifts have been measured for these phosphines, and show greater deviations from the values predicted by the first order additivity model than do those of more symmetrical phosphines (i.e., R3P and R2R'P).The shifts for these chiral molecules, and for a wide range of other phosphines, can be accurately predicted using a second order pairwise additivity scheme.The dependence of the observed and calculated chemical shifts upon electronegativity and steric factors is discussed.