51145-33-6

Upstream product

• 23708-48-7 pentamethylenebis(magnesium bromide) 
• 1499-21-4 Diphenylphosphinic chloride 
• 111-24-0 1,5-dibromo-pentane 
• 4559-70-0 Diphenylphosphine oxide 
• 22884-31-7 Hexa-P-phenyl-P,P'-pentanediyl-bis-phosphonium bromide 
• 1707-03-5 diphenyl-phosphinic acid 
• 111-29-5 1 ,5-pentanediol 
• 13360-92-4 phenyl diphenylphosphinite 
• 603-35-0 triphenylphosphine 

Relevant academic research and scientific papers

Evaluation of bifunctional chiral phosphine oxide catalysts for the asymmetric hydrosilylation of ketimines

A series of bifunctional phosphine oxides have been prepared and evaluated as catalysts for the trichlorosilane mediated asymmetric hydrosilylation of ketimines. bis-Phosphine oxides, hydroxy-phosphine oxides, and biaryl phosphine oxides all demonstrated good catalytic activity, but poor to moderate enantioselectivity. A bis-P-chiral phosphine oxide displayed the highest enantioselectivity of 60%.

Alcohol-based Michaelis-Arbuzov reaction: An efficient and environmentally-benign method for C-P(O) bond formation

The famous Michaelis-Arbuzov reaction is extensively used both in the laboratory and industry to manufacture tons of widely-used organophosphoryl compounds every year. However, this method and the modified Michaelis-Arbuzov reactions developed recently still have some limitations. We now report a new alcohol-version of the Michaelis-Arbuzov reaction that can provide an efficient and environmentally-benign method to address the problems of the known Michaelis-Arbuzov reactions. That is, a wide range of alcohols can readily react with phosphites, phosphonites, and phosphinites to give all the three kinds of phosphoryl compounds (phosphonates, phosphinates, and phosphine oxides) using an n-Bu4NI-catalyzed efficient C-P(O) bond formation reaction. This general method can also be easily scaled up and used for further synthetic transformations in one pot.

Understanding the structural properties of a homologous series of bis-diphenylphosphine oxides

A homologous series of bis-diphenylphosphine oxides (C6H5)2PO-(CH2)nPO(C 6H5)2 (with n = 2-8; denoted 2-8] have been investigated to explore the effects of a range of competing and cooperative intermolecular and intramolecular interactions on the structural properties in the solid state. The important factors influencing the structural properties include intramolecular aspects such as the conformation of the aliphatic chain and the intramolecular interaction between the two P=O dipoles in the molecule, and intermolecular aspects such as long-range electrostatic interactions (dominated by the arrangement of the P=O dipoles), C-H ... O interactions, C-H ... π interactions and π ... π interactions. Compounds 3 and 5 could be crystallized only as solvate co-crystals (3 · water and 5 · (toluene)2], whereas the crystal structures of all the other compounds contain only the bis-diphenylphosphine oxide molecule. The crystal structures have been determined from single-crystal X-ray diffraction data, with the exception of 7 (which has been determined here from powder X-ray diffraction data) and 4 (which was known previously). The compounds with even n represent a systematic structural series, exhibiting characteristic, essentially linear P=O ... P=O ... P=O dipolar arrays, together with C-H ... O and C-H ... π interactions. For the compounds with odd n, on the other hand, uniform structural behaviour is not observed across the series, although certain aspects of these crystal structures contribute in a general sense to our understanding of the structural properties of bis-diphenylphosphine oxides. Importantly, for the compounds with odd n, there is "frustration" with regard to the molecular conformation, as the preferred all-anti conformation of the aliphatic chain gives rise to an unfavourable parallel alignment of the two P=O dipoles within the molecule. Clearly the importance of avoiding a parallel alignment of the P=O dipoles becomes greater as n decreases. Local structural aspects (investigated by high-resolution solid-state 31P NMR spectroscopy) and thermal properties of the bis-diphenylphosphine oxide materials are also reported.

SYNTHESE ET STRUCTURE D'OXYDES ET DIOXYDES DE PHOSPHINES TERTIAIRES

Tertiary phosphine oxides have been prepared in excellent yield from primary alkyl halides and dihalides or aromatic halides and activated sodium phosphinates obtained by reaction of dialkyl phosphine oxides with complex bases (NaNH2/tBuONa).We have studied by 13C NMR the structure of these compounds.We have reported more particularly the influence of carbon atoms number between the two phosphorus in the case of dioxides and the influence of some parameters such as the temperature and the solvent on the NMR spectra.