- The lithiation reactivity and selectivity of differentially branched alkyldiphenylphosphine oxides - A simple and versatile approach to ortho-functionalized arylphosphine oxides
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Alkyldiphenylphosphine oxides typically undergo α-deprotonation with alkyllithium reagents. Here, the lithiation of differentially branched alkyldiphenylphosphine oxides was investigated and a diverse, but predictable reactivity was found. γ-Branched deri
- Mahamulkar, Shraddha G.,Císa?ová, Ivana,Jahn, Ullrich
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supporting information
p. 793 - 799
(2015/03/18)
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- Synthesis of phosphane oxides and phosphonates by cerium-mediated addition of organolithium compounds to chloro-phosphorus compounds
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The addition of organocerium reagents 2a-g to phosphinoyl chloride 1a or chlorophosphates 1b leads to the synthesis of phosphane oxides 3aa-ag and phosphonates 3bb, be in good to high yield. The reaction can be extended to cerium enolates 4 (of ketones) and 6 (of nitriles) except when a benzyl group bound to the carbonyl moiety should be metallated. The latter reaction is the first reported synthesis of β-oxophosphane oxides by a simple reaction between enolates and a phosphorus(V) halide.
- Dalpozzo, Renato,De Nino, Antonio,Miele, Daniela,Tagarelli, Antonio,Bartoli, Giuseppe
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p. 2299 - 2301
(2007/10/03)
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- The Reactions of Tris(trimethylsilyl)methyl-lithium with Some Carbon Electrophiles
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Tris(trimethylsilyl)methyl-lithium (1) reacts with non-enolisable aldehydes, ketones, and acid chlorides, and with some epoxides, with the formation of carbon-carbon bonds.This method of preparing functionalized silanes is limited by the readiness with which (1) abstracts a proton, if one is available, rather than attack at carbon.In the reaction with epoxides, the product alkoxide can transfer a silyl group from carbon to oxygen, and in one case the intermediate so formed reacts to give a cyclopropane (32) in what is a homologue of the Peterson reaction.The 1,4-transfer of a silyl group occurs in other systems when the resulting carbanion is stabilised by such groups as phenylthio and diphenylphosphinoyl.
- Fleming, Ian,Floyd, Christopher D.
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p. 969 - 976
(2007/10/02)
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