6002-48-8Relevant academic research and scientific papers
Alkylation of phosphine boranes by phase-transfer catalysis
Lebel, Helene,Morin, Sebastien,Paquet, Valerie
, p. 2347 - 2349 (2003)
(Matrix presented) The alkylation of phosphine boranes with various electrophiles proceeds with good to excellent yields in a biphasic solution in the presence of tetrabutylammonium bromide as a phase-transfer catalyst.
Sodium in liquid ammonia - A versatile tool in modifications of arylphosphine oxides
Stankevi?, Marek,W?odarczyk, Adam,Jaklińska, Magdalena,Parcheta, Renata,Pietrusiewicz, K. Micha?
experimental part, p. 8671 - 8678 (2011/12/03)
A simple and practical method for modifications of tertiary arylphosphine oxides based on their reaction with sodium in liquid ammonia is presented. Depending on the structure of the starting compounds, either dearomatisation of the phenyl substituent or cleavage of a P-aryl bond from phosphorus atom can be selectively performed and the corresponding (1,4-cyclohexadien-3-yl)phosphine oxides or secondary phosphine oxides were obtained in good to excellent yields.
Lewis acid catalyzed room-temperature Michaelis-Arbuzov rearrangement
Renard, Pierre-Yves,Vayron, Philippe,Leclerc, Eric,Valleix, Alain,Mioskowski, Charles
, p. 2389 - 2392 (2007/10/03)
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.
Reaction of metallated tert-butyl(phenyl)phosphane oxide with electrophiles as a route to functionalized tertiary phosphane oxides: Alkylation reactions
Haynes, Richard K.,Au-Yeung, Tin-Lok,Chan, Wai-Kuen,Lam, Wai-Lun,Li, Zhi-Yi,Yeung, Lam-Lung,Chan, Albert S. C.,Li, Pauline,Koen, Mark,Mitchell, Craig R.,Vonwiller, Simone C.
, p. 3205 - 3216 (2007/10/03)
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.
