128014-09-5

Upstream product

• 76380-86-4 S-methyl tert-butylphenylphosphinothiolate 
• 113502-18-4 P-(1,1-dimethylethyl)-P-phenylphosphinoselenoic acid Se-methyl ester 
• 6057-79-0 (S)-(-)-t-butyl(phenyl)phosphine oxide 
• 4923-86-8 t-butyl(phenyl)phosphinic acid 
• 1940-57-4 9H-fluoren-9-yl bromide 
• 4923-85-7 tert-butylphenylphosphinic acid chloride 
• 51584-29-3 (R)-(+)-S-methyl tert-butylphenylphosphinothiolate 
• 644-97-3 Dichlorophenylphosphine 
• 98976-30-8 tert-Butylphenylphosphine oxide 

Downstream Products

• 302902-40-5 C₁₇H₂₂NOP 
• 1225274-83-8 (+/-)-P-t-butyl-P-phenyl-N-phosphinoyl benzaldimine 
• 1323157-06-7 C₁₇H₁₅F₅NOP 
• 1323157-07-8 C₂₀H₂₆NO₄P 
• 1323157-08-9 C₁₈H₁₉N₂OP 
• 51028-18-3 (+/-)-P-t-butyl-P-phenyl-N-phosphoramidate 

Relevant academic research and scientific papers

The synthesis and reactivity of phosphinous acid-boranes

Phosphinic acid chlorides are converted directly into phosphinous acid-boranes in a process utilizing BH3-THF complex as a reducing agent. The process is general and affords phosphinous acid-boranes in good to very high yields. Phosphinous acid

Stereoselective addition of grignard reagents to new P-chirogenic N-phosphinoylbenzaldimines: Effect of the phosphorus substituents on the stereoselectivity

Several phosphinoylimines have been synthesized in five steps by starting from the appropriate phosphane oxide and were then treated with methylmagnesium bromide to give both diastereoisomers in high yields and with promising diastereomeric ratios. Then N-[(tert-butyl)(phenyl)phosphinoyl]benzaldimine, which displayed the best results, was subjected to the 1,2-addition of various Grignard reagents to evaluate the best chiral induction due to the stereogenic phosphorus atom. The corresponding adducts were obtained in excellent yields and with moderate to excellent diastereoisomeric ratios. Copyright

Stereoselective addition of Grignard reagents to new P-chirogenic N-phosphinoylimines

The addition of various Grignard reagents to P-t-butyl-P-phenyl-N- phosphinoyl benzaldimine provides a stereoselective method for the synthesis of chiral phosphinoylamines. The Royal Society of Chemistry.

New look into the synthesis of polyhalogenoarylphosphanes

The present study shows new aspects of the synthesis of polyhalogenoarylphosphanes. The sterically hindered anions Ph(R)P-Y- (1a-c, Y = O, lone pair; R = Ph, But) have been used to show the complexity of the reaction between phosphorus nucleophiles and hexahalogenobenzenes or 9-bromofluorene (E3). The Ph(But)P-O-(1a) anion reacts with hexachlorobenzene (E1), hexafluorobenzene (E2), or E3 to give Ph(R)P(O)X (4a-c, X = F, Cl, Br) with the release of the corresponding carbanion as a nucleofuge, followed by side reactions. In contrast, the lithium phosphides Ph(R)PLi (1b,c) react with hexahalogenobenzenes to give the corresponding diphosphanes 5a,b as the main product and traces of P-arylated products, i.e., Ph(R)P-C6X 5 (10a,b, X = Cl, F). Unexpectedly, Ph(But)PLi (1b) reacts with an excess of 9-bromofluorene to give only halogenophosphane Ph(Bu t)P-X. Taylor & Francis Group, LLC.

New approaches to the synthesis of diphosphine dioxides and hypophosphoric acid esters

An union >P-O- has been applied as an efficient synthetic precursor of four coordination compounds of the R2P(O)-(O)PR 2 type, namely diphosphine dioxides (R = alkyl, aryl) as well as hypophosphoric acid esters (R = alkoxy, aryloxy), in a one-pot reaction. Furthermore, there were elaborated some mechanistic aspects of the origin of the >P(O)-O-(O)PP-O- and >P(O)X (X= Cl, Br) electrophiles. Attention is focused on the synthesis of the >P(O)-(O)P compounds.

Reaction of metallated tert-butyl(phenyl)phosphane oxide with electrophiles as a route to functionalized tertiary phosphane oxides: Alkylation reactions

P-Chiral tertiary phosphane oxides have been prepared from each of the secondary phosphane oxides racemic 1, (S(p))-(-)-4 and (Rp)-(+)-tert-butylphenylphosphane oxide (5) by lithiation with LDA or nBuLi, or sodiation with sodium hydride, in THF, and then by treatment with a series of primary alkyl halides. Doubly P-chiral ditertiary bis(phosphane oxides) are also obtained from these metallated secondary phosphane oxides by treatment with electrophiles based on straight-chain, tartrate-derived, and bishalomethylarene dihalides. In general, the bis-phosphane oxides are obtained in good yields. However, when the α,ω-dihalide bears an embedded heteroatom (O or Si), yields are diminished. The enantiomeric purity of each of the products was assessed through admixture with (R(p))- and (S(p))-tert-butyl(phenyl)phosphanylthioic acids and measurement of the tert-butyl resonances in the 1H-NMR spectra. In all cases, the act of metallation of the enantiomerically pure secondary phosphane oxide followed by its alkylation is not accompanied by detectable racemization. This method for preparing P-chiral tertiary phosphane oxides is therefore more straightforward than those described previously.

The first examples of enantiomerically pure diphosphane dioxides-(R(P),R(P))- and (S(P),S(P))-1,2-di-tert-butyl-1,2-diphenyldiphosphane 1,2-dioxides, and (R(P))- and (Sp)-1-tert-butyl-1,2,2-triphenyldiphosphane 1,2-dioxides

Whereas oxidative dimerization of each of the lithiated reagents (R(P))- and (S(P))-tert-butylphenylphosphane oxides 1 Li and 2 Li by means of oxygen in THF at low temperature led cleanly to meso-1,2-di-tert-butyl-1,2-diphenyldiphosphane dioxide (3), the respective nucleophilic substitution reactions of 1 Li and 2 Li with the (R(P))- and (S(P))-tert-butylphenylphosphinic bromides (4 and 6) in THF under argon led to the corresponding (S(P),S(P))-and (R(P),R(P))-1,2-di-tert-butyl-1,2-diphenyldiphosphane dioxides (5 and 7) in good yields together with the meso-diphosphane dioxide 3. The structures of 3 and 5 were established by X-ray crystallography. Similarly, the reaction of lithiated (R(P))-phosphane oxide 1 Li with diphenylphosphinic bromide (8) or of achiral lithiated diphenylphosphane oxide 10 Li with (R(P))-tert-butylphenylphosphinic bromide (4) provided (S(P))-tert-butyltriphenyldiphosphane dioxide (9).

Preparation of bi- and tridentate doubly P-chiral diphosphine dioxide ligands for asymmetric catalysis

Syntheses of bi-and tridentate doubly P-chiral diphosphine dioxides through reaction of the individual enantiomers of optically pure lithiated tert-butylphenylphosphine oxide with different bifunctional electrophiles are described.

Reaction of Thiolo and Selenolo Esters of Phosphorus Acids with Halogens. Part 2. Interaction of S-Methyl t-Butyl(phenyl)- and Di-t-butyl-phosphinothiolates with Elemental Bromine and Iodine

The reaction of S-methyl t-butyl(phenyl)- and di-t-butyl-phosphinothiolates with bromine and iodine involves the transient formation of the same type of halosulphonium salts, ButRP(O)S+(X)MeX- and phosphonium salts, Busup

REACTION OF SELENOESTERS OF PHOSPHORUS ACIDS WITH HALOGENS

Reaction of phosphinoselenoates 1a-b with elemental chlorine, bromine, iodine as well as sulfuryl chloride involves halogenolysis of P-Se bond and formation of tert-butylphenylphosphinohalogenate 7.Intermediate products, containing one and two phosphorus atoms were detected by 31P NMR.The similarities and differences in the behavior of phosphorus selenoesters and their thio-analogues are discussed.