Alistair I. Longshaw, Michael W. Carland, E. Krenske
Aug 6, 2007
Citations
0
Influential Citations
6
Citations
Journal
Tetrahedron Letters
Abstract
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) 3 CH does not reduce organohalides. In competition experiments between (TMS) 3 CH and the poor chain mediator Et 3 SiH, the latter performed the reduction. Computational investigations support these experimental findings and indicate that the C–H bond of (TMS) 3 CH is too strong for this compound to serve as an effective mediator of radical reactions.