21448-79-3Relevant articles and documents
Synthesis and properties of tert-butylphenylmethylene(chloro)phosphorane
Kolodyazhna,Grishkun,Sheiko,Kolodyazhna,Kolodyazhnyi
, p. 1639 - 1643 (2015)
The synthesis and properties of tert-butylphenylmethylene(chloro)phosphorane were described. The prepared chlorophosphorane reacted with alcohols and phenol with the formation of the corresponding phosphonium salts. Its reaction with carbonyl compounds le
Synthesis of Optically Active Phosphorus Compounds via Metal Phosphinites Generated by Reaction of Optically Active Selenophosphinates with Phenyllithium
Kawashima, Takayuki,Iwanaga, Hiroki,Okazaki, Renji
, p. 1531 - 1532 (1993)
Sequential treatment of optically active Se-benzyl t-butylphenylselenophosphinate with PhLi and then with electrophiles such as alkyl halides elemental selenium gave optically active phosphorus compounds in good chemical and optical yields with a retention of configuration at phosphorus atom, together with benzyl phenyl selenide.
Stereoselectivity of Michael Addition of P(X)-H-Type Nucleophiles to Cyclohexen-1-ylphosphine Oxide: The Case of Base-Selective Transformation
Jaklińska, Magdalena,Cordier, Marie,Stankevi?, Marek
, p. 1378 - 1390 (2016)
Michael addition of phosphorus nucleophiles to the unsymmetrically substituted tert-butyl(1,4-cyclohexadien-3-yl)phosphine oxide and its derivatives has been described. The addition proceeds with the formation of the mixture of two isomeric products with good yield and diastereoselectivity. The reaction of tert-butyl(cyclohexen-1-yl)methylphosphine oxide with phosphorus nucleophiles is base sensitive and might afford two epimers which differ at one chirality center. The absolute configuration of the products has been assigned on the basis of conformational and 1H NMR analysis, and the mechanism of the reaction has been discussed. The Michael addition of phosphorus nucleophiles is postulated to proceed with or without consecutive epimerization of two α-carbanions.
Scalable Enantiomeric Separation of Dialkyl-Arylphosphine Oxides Based on Host–Guest Complexation with TADDOL-Derivatives, and their Recovery
Bagi, Péter,Fogassy, Elemér,Herbay, Réka,Holczbauer, Tamás,Keglevich, Gy?rgy,Mátrav?lgyi, Béla,Madarász, János,Székely, Gy?rgy,Varga, Bence
supporting information, (2020/03/23)
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.
