Tris(trimethylsilyl)methane is not an effective mediator of radical reactions |
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| Authors: | Alistair I. Longshaw Michael S. Sherburn |
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| Affiliation: | ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra ACT 0200, Australia |
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| 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: | Radicals Synthetic methods Ab initio calculations |
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