| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5276556 | Tetrahedron Letters | 2007 | 4 Pages |
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.
Graphical abstractA joint experimental-computational investigation shows that (TMS)3CH is not a useful radical reducing agent.Download full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Alistair I. Longshaw, Michael W. Carland, Elizabeth H. Krenske, Michelle L. Coote, Michael S. Sherburn,