Sodium and potassium derivatives of diphenyl(trimethylsilyl)methane

Michael S. Hill; Peter B. Hitchcock

doi:10.1016/S0022-328X(02)01982-4

Sodium and potassium derivatives of diphenyl(trimethylsilyl)methane

Michael S. Hill, Peter B. Hitchcock

University of Sussex

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

12 Citations (SciVal)

Abstract

Base-free sodium and potassium derivatives of Ph₂(Me₃Si)CH have been synthesised from the substituted diphenylmethane and a 'superbase' mixture of ⁿBuLi/^tBuOM (M = Na or K) in hexane. Multinuclear NMR studies have demonstrated that the resultant carbanions are highly delocalised in THF-d₈ solution. Crystalline PMDETA (PMDETA = N,N,N′,N″,N″-pentamethyldiethylenetriamine) adducts of both the sodium and potassium diphenylmethyl anions have been isolated from toluene solution and the crystal structure of the sodium derivative has been determined. This exists as a monomeric molecular species with η³-coordination of sodium to the carbanion, which is almost planar (Σ_angles = 358.6°) at the central methyl carbon.

Original language	English
Pages (from-to)	182-187
Number of pages	6
Journal	Journal of Organometallic Chemistry
Volume	664
Issue number	1-2
DOIs	https://doi.org/10.1016/S0022-328X(02)01982-4
Publication status	Published - 16 Dec 2002

Keywords

Bulky ligands
Diphenylmethyl
Potassium
Sodium

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0022-328X(02)01982-4

Cite this

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abstract = "Base-free sodium and potassium derivatives of Ph2(Me3Si)CH have been synthesised from the substituted diphenylmethane and a 'superbase' mixture of nBuLi/tBuOM (M = Na or K) in hexane. Multinuclear NMR studies have demonstrated that the resultant carbanions are highly delocalised in THF-d8 solution. Crystalline PMDETA (PMDETA = N,N,N′,N″,N″-pentamethyldiethylenetriamine) adducts of both the sodium and potassium diphenylmethyl anions have been isolated from toluene solution and the crystal structure of the sodium derivative has been determined. This exists as a monomeric molecular species with η3-coordination of sodium to the carbanion, which is almost planar (Σangles = 358.6°) at the central methyl carbon.",

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T1 - Sodium and potassium derivatives of diphenyl(trimethylsilyl)methane

AU - Hill, Michael S.

AU - Hitchcock, Peter B.

PY - 2002/12/16

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N2 - Base-free sodium and potassium derivatives of Ph2(Me3Si)CH have been synthesised from the substituted diphenylmethane and a 'superbase' mixture of nBuLi/tBuOM (M = Na or K) in hexane. Multinuclear NMR studies have demonstrated that the resultant carbanions are highly delocalised in THF-d8 solution. Crystalline PMDETA (PMDETA = N,N,N′,N″,N″-pentamethyldiethylenetriamine) adducts of both the sodium and potassium diphenylmethyl anions have been isolated from toluene solution and the crystal structure of the sodium derivative has been determined. This exists as a monomeric molecular species with η3-coordination of sodium to the carbanion, which is almost planar (Σangles = 358.6°) at the central methyl carbon.

AB - Base-free sodium and potassium derivatives of Ph2(Me3Si)CH have been synthesised from the substituted diphenylmethane and a 'superbase' mixture of nBuLi/tBuOM (M = Na or K) in hexane. Multinuclear NMR studies have demonstrated that the resultant carbanions are highly delocalised in THF-d8 solution. Crystalline PMDETA (PMDETA = N,N,N′,N″,N″-pentamethyldiethylenetriamine) adducts of both the sodium and potassium diphenylmethyl anions have been isolated from toluene solution and the crystal structure of the sodium derivative has been determined. This exists as a monomeric molecular species with η3-coordination of sodium to the carbanion, which is almost planar (Σangles = 358.6°) at the central methyl carbon.

KW - Bulky ligands

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KW - Potassium

KW - Sodium

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Sodium and potassium derivatives of diphenyl(trimethylsilyl)methane

Abstract

Keywords

ASJC Scopus subject areas

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