Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/29699
Title: Reaction of metallated tert-butyl(phenyl)phosphane oxide with electrophiles as a route to functionalized tertiary phosphane oxides : Alkylation reactions
Authors: Haynes, RK
Au Yeung, TL
Chan, WK
Lam, WL
Li, ZY
Yeung, LL
Chan, ASC
Li, P 
Koen, M
Mitchell, CR
Vonwiller, SC
Keywords: Alkylations
Halides
Metallations
P-Chiral phosphane oxides
Issue Date: 2000
Source: European journal of organic chemistry, 2000, v. , no. 18, p. 3205-3216 How to cite?
Journal: European Journal of Organic Chemistry 
Abstract: 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.
URI: http://hdl.handle.net/10397/29699
ISSN: 1434-193X
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