17170-48-8

Upstream product

• 13153-92-9 (+)-(R)-methyl-n-propylphenylphosphine sulphide 
• 80677-32-3 C₁₀H₁₇NP⁽¹⁺⁾ 
• 425-75-2 trifluoromethanesulfonic acid ethyl ester 
• 701-03-1 methylpropylphenylphosphine 
• 701-03-1 (+)-(S)-methyl-n-propyl phenylphosphine 
• 4653-63-8 methyl-phenyl-propyl-phosphine oxide 
• 114026-76-5 (-)-(2R,3R)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro[4.5]decane 
• 2946-61-4 phenylphosphonous acid dimethyl ester 
• 644-97-3 Dichlorophenylphosphine 
• 6389-79-3 methyl methylphenylphosphinate 

Downstream Products

• 839-28-1 R(-)-Benzyl-methyl-phenyl-n-propyl-phosphoniumbromid 
• 13153-92-9 (+)-(R)-methyl-n-propylphenylphosphine sulphide 
• 1515-99-7 (S)-(-)-Methylphenyl-n-propylphosphanoxid 
• 701-03-1 (-)-(R)-methyl-n-propylphenylphosphine 

Relevant academic research and scientific papers

Unprecedented Base Effect On the Synthesis of Chiral Phosphinate Esters: A New Route to P-Chiral Phosphine Oxides of High Enantiomeric Purity

The stereochemical outcome of the reaction of chiral secondary alcohols with a phosphinyl chloride was found to be highly dependent on the achiral base used.Thus, the reaction of the readily available sugar derived carbinols, 1 and 2, with methylphenylpho

Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery

Several dialkyl-arylphosphine oxides were prepared, and the enantioseparation of the corresponding racemates was elaborated with host–guest complexation using TADDOL-derivatives. The crystallization conditions were optimized and two separate crystallization methods, one in organic solvent, and the other in water, were found to yield five examples of phosphine oxides with enantiomeric excess values higher than 94 %. A gram scale resolution was performed, and both enantiomers of the methyl-phenyl-propyl-phosphine oxide were separated with (R,R)- or (S,S)-spiro-TADDOL. The intermolecular interactions responsible for the enantiomeric recognition between the chiral host and guest molecules were investigated by single-crystal X-ray diffractional structural determinations. The similarities in the structural patterns of a few diastereomeric crystals were checked by powder X-ray diffraction, as well. Organic solvent nanofiltration (OSN) was used as a scalable technique for the decomposition of the corresponding phosphine oxide–spiro-TADDOL molecular complexes, and for the recovery of the phosphine oxide enantiomers and resolving agents.

Stereoselective catalytic synthesis of P-stereogenic oxides via hydrogenative kinetic resolution

A highly stereoselective catalytic method for the preparation of structurally diverse P-stereogenic oxides has been developed. The approach relies on the ability of rhodium complexes derived from an enantiopure P-OP ligand to kinetically resolve racemic α,β-unsaturated phosphane oxides by hydrogenation of the C= C motif and formation of highly enantioenriched (or even enantiopure) P-stereogenic oxides. The practicality of the methodology has been demonstrated by the preparation of potentially functional P-chiral molecules for catalytic enantioselective synthesis.

PALLADIUM-CATALYZED SYNTHESIS OF CHIRAL, NONRACEMIC ISOPROPYL ARYLMETHYLPHOSPHINATES

An efficient, new synthesis of enantiomerically pure functionalized isopropyl arylmethylphosphinates via palladium-catalyzed formation of C-P bond is presented.

The Mechanisms of the Conversion of Thiophosphoryl Compounds into their Phosphoryl Analogues by Photochemically Excited 3-Methylpyridazine 2-Oxide and by 2-Methyl-3-p-nitrophenyloxaziridine; a Comparison

Reactions of tri-p-substituted triarylphosphine sulphides with 3-methylpyridazine 2-oxide, under photolysis, and with 2-methyl-3-p-nitrophenyloxaziridine both give the corresponding phosphine oxides.A detailed study and comparison of the two reactions shows that they are mechanistically quite distinct and that it is unlikely that the active oxygenating species generated by photolysis of the N-oxide, which attacks the phosphine sulphides, is an oxaziridine.The evidence presented suggests that this species may in fact be 'oxene'.

PREPARATION OF OPTICALLY ACTIVE PHOSPHINE OXIDES BY REGIOSELECTIVE CLEAVAGE OF CYCLIC PHENYLPHOSPHONITE WITH ALKYL HALIDES

The Arbuzov reaction of (2S,4S)-methyl-2-phenyl-1,3,2-dioxaphosphorinane with various alkyl halides gave the diastereomerically pure phosphinates with regioselective cleavage of the primary carbon-oxygen bond.These phosphinates reacted with Grignard reage

PHOSPHORORGANISCHE VERBINDUNGEN 103. Die ozonolytische Desulfurierung von Thiophosphorylverbindungen: P=S -> P=O

The sulfur atom in thiophosphorylgroups P=S is exchanged by oxygen with retention of configuration according to (1) and (2) as a result of an interaction of the P=S groups with ozone (Table 1 and 2).In dithiophosphinicacidesters only the thionosulfur is easily replaced by oxygen using ozone.The absolute configuration of the enantiomeric methyl-phenyl-phosphinicacid-p-nitrophenylesters 7 an 8 is controlled on the basis of the reaction circle (4).Serine enzymes are blocked by the phosphinicacidesters 7 and 8 by a rate factor of about 60 faster than by the corresponding thionophosphinicacidesters 5 and 6.The phosphinicacidesters 7 (and 8) have a high O-selectivity in competing reactions (7:n-BuOH:n-BuNH2 = 1:1:1) in contrast to the thionophosphinicacidesters 5 (and 6) with no selectivity (ester:amide = 4:6).

Mechanisms in Electrophilic Reactions of Reactive Nitrogen Compounds with Phosphanes

Chiral phosphanes were used as nucleophiles in reactions with reactive nitrogen compounds to investigate the mechanisms by stereochemical means:a) Retention on phosphorus occurs in the amination with O-(mesitylsulfonyl)hydroxylamine consistent with a Ssu