23896-93-7

Upstream product

• 98-86-2 acetophenone 
• 829-85-6 diphenylphosphane 
• 134920-71-1 1-Diphenylphosphinoxy-1-phenylethan 
• 75-00-3 chloroethane 
• 71-43-2 benzene 
• 55894-16-1 (2-methoxyethyl)triphenylphosphonium bromide 
• 791-28-6 Triphenylphosphine oxide 
• 19115-00-5 sodium salt of diphenyl phosphine oxide 
• 672-65-1 (1-chloroethyl)benzene 
• 2959-74-2 benzyldiphenylphosphine oxide 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 4559-70-0 Diphenylphosphine oxide 
• 96-09-3 styrene oxide 
• 1079-66-9 chloro-diphenylphosphine 

Downstream Products

• 130613-41-1 2-(Diphenyl-phosphinoyl)-2-phenyl-propionaldehyde 
• 55640-98-7 (S)-diphenyl-(1-phenyl-ethyl)-phosphane oxide 
• 159406-55-0 (R)-diphenyl-(1-phenyl-ethyl)-phosphane oxide 
• 130613-50-2 (S)-5-(Diphenyl-phosphinoyl)-1,5-diphenyl-hexane-3,4-diol 
• 130613-50-2 (3R,4S,5S)-5-(Diphenyl-phosphinoyl)-1,5-diphenyl-hexane-3,4-diol 

Relevant academic research and scientific papers

METHOD FOR PRODUCING ORGANOPHOSPHORUS COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an organophosphorus compound which has excellent energy efficiency without containing a halogenated alkyl or a by-product derived from a halogenated alkyl. SOLUTION: There is provided a method for producing an organophosphorus compound by reacting a trivalent organophosphorus compound represented by the following general formula (1) in the presence of a super strong acid and/or at least one acid catalyst containing a solid superstrong acid catalyst to generate a pentavalent organophosphorus compound represented by the following general formula. (where Z1 represents OR2 or R2; Z2 represents OR3 or R3; R1, R2 and R3 represent an alkyl group, an alkenyl group or the like; when R2 and R3 are an alkyl group or the like, R2 and R3 may be bonded to each other to form a cyclic structure; and R1 may be a hydrogen atom.) SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Selective C-P(O) Bond Cleavage of Organophosphine Oxides by Sodium

Sodium exhibits better efficacy and selectivity than Li and K for converting Ph3P(O) to Ph2P(OM). The destiny of PhNa co-generated is disclosed. A series of alkyl halides R4X and aryl halides ArX all react with Ph2P(ONa) to produce the corresponding phosphine oxides in good to excellent yields.

Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds

Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.

Reductive coupling reactions: A new strategy for C(sp3)-P bond formation

The C(sp3)-P bond forming reaction utilizing N-tosylhydrazones as readily available alkylating reagents was developed, which provides a new opportunity for preparing phosphine oxide derivatives with moderate to good yields. This reductive coupling reaction is proposed to proceed through an insertion of copper carbene into P-H bond of H-phosphorus oxides. The salient features of the reaction are operational simplicity and functional-group tolerance.

A novel copper-catalyzed reductive coupling of N-tosylhydrazones with H-phosphorus oxides

We report here a novel C(sp3)-P bonds formation via copper-catalyzed reductive coupling of N-tosylhydrazones with H-phosphorus oxides. A variety of aliphatic and aromatic substrates bearing electron-rich and electron-deficient substituents affords phosphine oxide derivatives with moderate to good yields. This work suggests a new transformation of aldehydes/ketones via N-tosylhydrazones to organophosphorus compounds.

Ph2PI as a reduction/phosphination reagent: Providing easy access to phosphine oxides

The reaction of aldehydes with Ph2PI provides a facile way to the synthesis of pentavalent phosphine compounds with moderate to good yields.

Synthesis of phosphorus based ligands

Chiral ligands of the formula I or II, may be obtained in high enantiomeric purity from compounds of the formulae III or IV, respectively, with suitable phosphines, where the symbols R1, R, n, R3, R4, R' are as described i

Trimethylsilyl halide-promoted Michaelis-Arbuzov rearrangement

(Matrix presented) We describe a new, straightforward, and easy-to-handle method for achieving an unprecedented trimethylsilyl halide-catalyzed Michaelis-Arbuzov-like rearrangement. This rearrangement occurs at temperatures from room temperature to 80°C and does not require addition of any alkyl halide. The scope and limitations of this new reaction are explored, as well as its mechanism.

Lewis acid catalyzed room-temperature Michaelis-Arbuzov rearrangement

The taming of the shrew! For the first time, a broadly applicable efficient room-temperature Arbuzov rearrangement is described. This reaction is accomplished through an atom-economical Lewis acid catalyzed process (see scheme, TMSOTf=trimethylsilyl trifluoromethane-sulfonate). The method has been generalized to primary and activated secondary phosphites, phosphinites, and phosphonites.

ALKALINE HYDROLYSIS OF β AND γ-FUNCTIONAL PHOSPHONIUM SALTS

A model study of alkaline hydrolysis of β- and γ-heterosubstituted phosphonium salts has been made and used as a synthetic method to obtain diphosphine dioxides affording additional coordination sites in an alkyl chain linked to phosphorus.After synthesis of the corresponding salts, anomalous fragmentations, such as inversion in cleavage selectivity or participation of the reaction solvent, have been pointed out in alkaline hydrolysis of β-functional phosphonium salts.A mechanism is suggested to account for the presence of all compounds detected.In the case of γ-functional phosphonium salts, the alkaline hydrolysis leads only to predicted compounds corresponding to the usual selective cleavage of one phenyl group.The results observed have been used to synthesize symmetric and asymmetric diphosphine dioxides with ether substituted side chains. - Key words: Phosphonium salt, phosphine oxide, diphosphine dioxides, alkaline hydrolysis, cleavage, mechanism.