Tris(trimethylsilyl)methane is not an effective mediator of radical reactions
Date
2007
Authors
Longshaw, Alistair
Carland , Michael
Krenske, Elizabeth
Coote, Michelle
Sherburn, Michael
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Volume Title
Publisher
Elsevier
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.
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Keywords
Keywords: adamantane derivative; methane; organohalogen derivative; trimethylsilyl derivative; tris(trimethylsilyl)methane; unclassified drug; article; chemical bond; chemical reaction kinetics; dehalogenation; mathematical analysis; reaction analysis; reduction; t Ab initio calculations; Radicals; Synthetic methods
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Source
Tetrahedron Letters
Type
Journal article
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2037-12-31