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

Longshaw, Alistair; Carland , Michael; Krenske, Elizabeth; Coote, Michelle; Sherburn, Michael

Description

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...[Show more]

CollectionsANU Research Publications
Date published: 2007
Type: Journal article
URI: http://hdl.handle.net/1885/28283
Source: Tetrahedron Letters
DOI: 10.1016/j.tetlet.2007.06.055

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