Lithiations of phosphane oxides

David R. Armstrong; Robert P. Davies; Lorraine Dunbar; Paul R. Raithby; Ronald Snaith; Andrew E.H. Wheatley

doi:10.1080/10426509708046761

Lithiations of phosphane oxides

David R. Armstrong
, Robert P. Davies
, Lorraine Dunbar
, Paul R. Raithby
, Ronald Snaith
, Andrew E.H. Wheatley

University of Strathclyde
University of Cambridge

Research output: Contribution to journal › Article › peer-review

7 Citations (SciVal)

Abstract

Two studies on lithiated phosphane oxides (Horner-Wittig reagents) are reported. In the first, attempted deprotonation of Ph₂P(O)CH₃ using the lithium amide (Me₃Si)₂NLi leads merely to an adduct between the two species and suggests thereby an initiation step for many lithiation reactions. The mechanism and energetics of deprotonation have been studied further by ab initio MO calculations on the model system H₂P(O)CH₃ + H₂NLi. In a related study the phosphane oxide Ph₂P(O)CH₂CHMeEt has been successfully lithiated in non-Lewis base media, affording a tetrameric (LiO)₄ cubane structure whose key feature is the presence of Li-C bonds.

Original language	English
Pages (from-to)	51-62
Number of pages	12
Journal	Phosphorus, Sulfur and Silicon and Related Elements
Volume	124
DOIs	https://doi.org/10.1080/10426509708046761
Publication status	Published - 1 Jan 1997

Keywords

Lithiations
Phosphane oxides
X-ray structures

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

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10.1080/10426509708046761

Cite this

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title = "Lithiations of phosphane oxides",

abstract = "Two studies on lithiated phosphane oxides (Horner-Wittig reagents) are reported. In the first, attempted deprotonation of Ph2P(O)CH3 using the lithium amide (Me3Si)2NLi leads merely to an adduct between the two species and suggests thereby an initiation step for many lithiation reactions. The mechanism and energetics of deprotonation have been studied further by ab initio MO calculations on the model system H2P(O)CH3 + H2NLi. In a related study the phosphane oxide Ph2P(O)CH2CHMeEt has been successfully lithiated in non-Lewis base media, affording a tetrameric (LiO)4 cubane structure whose key feature is the presence of Li-C bonds.",

keywords = "Lithiations, Phosphane oxides, X-ray structures",

author = "Armstrong, \{David R.\} and Davies, \{Robert P.\} and Lorraine Dunbar and Raithby, \{Paul R.\} and Ronald Snaith and Wheatley, \{Andrew E.H.\}",

year = "1997",

month = jan,

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doi = "10.1080/10426509708046761",

language = "English",

volume = "124",

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publisher = "Taylor and Francis",

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TY - JOUR

T1 - Lithiations of phosphane oxides

AU - Armstrong, David R.

AU - Davies, Robert P.

AU - Dunbar, Lorraine

AU - Raithby, Paul R.

AU - Snaith, Ronald

AU - Wheatley, Andrew E.H.

PY - 1997/1/1

Y1 - 1997/1/1

N2 - Two studies on lithiated phosphane oxides (Horner-Wittig reagents) are reported. In the first, attempted deprotonation of Ph2P(O)CH3 using the lithium amide (Me3Si)2NLi leads merely to an adduct between the two species and suggests thereby an initiation step for many lithiation reactions. The mechanism and energetics of deprotonation have been studied further by ab initio MO calculations on the model system H2P(O)CH3 + H2NLi. In a related study the phosphane oxide Ph2P(O)CH2CHMeEt has been successfully lithiated in non-Lewis base media, affording a tetrameric (LiO)4 cubane structure whose key feature is the presence of Li-C bonds.

AB - Two studies on lithiated phosphane oxides (Horner-Wittig reagents) are reported. In the first, attempted deprotonation of Ph2P(O)CH3 using the lithium amide (Me3Si)2NLi leads merely to an adduct between the two species and suggests thereby an initiation step for many lithiation reactions. The mechanism and energetics of deprotonation have been studied further by ab initio MO calculations on the model system H2P(O)CH3 + H2NLi. In a related study the phosphane oxide Ph2P(O)CH2CHMeEt has been successfully lithiated in non-Lewis base media, affording a tetrameric (LiO)4 cubane structure whose key feature is the presence of Li-C bonds.

KW - Lithiations

KW - Phosphane oxides

KW - X-ray structures

UR - https://www.scopus.com/pages/publications/0347704231

U2 - 10.1080/10426509708046761

DO - 10.1080/10426509708046761

M3 - Article

AN - SCOPUS:0347704231

SN - 1042-6507

VL - 124

SP - 51

EP - 62

JO - Phosphorus, Sulfur and Silicon and Related Elements

JF - Phosphorus, Sulfur and Silicon and Related Elements

ER -

Lithiations of phosphane oxides

Abstract

Keywords

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