Tris(trimethylsilyl)methane is not an effective mediator of radical reactions

Alistair I. Longshaw; Michael W. Carland; Elizabeth H. Krenske; Michelle L. Coote; Michael S. Sherburn

doi:10.1016/j.tetlet.2007.06.055

Tris(trimethylsilyl)methane is not an effective mediator of radical reactions

Alistair I. Longshaw, Michael W. Carland, Elizabeth H. Krenske, Michelle L. Coote^*, Michael S. Sherburn

^*Corresponding author for this work

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

10 Citations (Scopus)

Abstract

The reductive dehalogenation of organohalides by tris(trimethylsilyl)methane has been re-investigated. Contrary to claims made in a recent publication (Tetrahedron Lett. 2006, 47, 5163-5165), (TMS)₃CH does not reduce organohalides. In competition experiments between (TMS)₃CH and the poor chain mediator Et₃SiH, the latter performed the reduction. Computational investigations support these experimental findings and indicate that the C-H bond of (TMS)₃CH is too strong for this compound to serve as an effective mediator of radical reactions.

Original language	English
Pages (from-to)	5585-5588
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2007.06.055
Publication status	Published - 6 Aug 2007

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10.1016/j.tetlet.2007.06.055

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title = "Tris(trimethylsilyl)methane is not an effective mediator of radical reactions",

abstract = "The reductive dehalogenation of organohalides by tris(trimethylsilyl)methane has been re-investigated. Contrary to claims made in a recent publication (Tetrahedron Lett. 2006, 47, 5163-5165), (TMS)3CH does not reduce organohalides. In competition experiments between (TMS)3CH and the poor chain mediator Et3SiH, the latter performed the reduction. Computational investigations support these experimental findings and indicate that the C-H bond of (TMS)3CH is too strong for this compound to serve as an effective mediator of radical reactions.",

keywords = "Ab initio calculations, Radicals, Synthetic methods",

author = "Longshaw, {Alistair I.} and Carland, {Michael W.} and Krenske, {Elizabeth H.} and Coote, {Michelle L.} and Sherburn, {Michael S.}",

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T1 - Tris(trimethylsilyl)methane is not an effective mediator of radical reactions

AU - Longshaw, Alistair I.

AU - Carland, Michael W.

AU - Krenske, Elizabeth H.

AU - Coote, Michelle L.

AU - Sherburn, Michael S.

PY - 2007/8/6

Y1 - 2007/8/6

N2 - The reductive dehalogenation of organohalides by tris(trimethylsilyl)methane has been re-investigated. Contrary to claims made in a recent publication (Tetrahedron Lett. 2006, 47, 5163-5165), (TMS)3CH does not reduce organohalides. In competition experiments between (TMS)3CH and the poor chain mediator Et3SiH, the latter performed the reduction. Computational investigations support these experimental findings and indicate that the C-H bond of (TMS)3CH is too strong for this compound to serve as an effective mediator of radical reactions.

AB - The reductive dehalogenation of organohalides by tris(trimethylsilyl)methane has been re-investigated. Contrary to claims made in a recent publication (Tetrahedron Lett. 2006, 47, 5163-5165), (TMS)3CH does not reduce organohalides. In competition experiments between (TMS)3CH and the poor chain mediator Et3SiH, the latter performed the reduction. Computational investigations support these experimental findings and indicate that the C-H bond of (TMS)3CH is too strong for this compound to serve as an effective mediator of radical reactions.

KW - Ab initio calculations

KW - Radicals

KW - Synthetic methods

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DO - 10.1016/j.tetlet.2007.06.055

M3 - Article

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VL - 48

SP - 5585

EP - 5588

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Tris(trimethylsilyl)methane is not an effective mediator of radical reactions

Abstract

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