Tris(trimethylsilyl)methane is not an effective mediator of radical reactions
Date
Authors
Longshaw, Alistair
Carland , Michael
Krenske, Elizabeth
Coote, Michelle
Sherburn, Michael
Journal Title
Journal ISSN
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.
Description
Citation
Collections
Source
Tetrahedron Letters
Type
Book Title
Entity type
Access Statement
License Rights
Restricted until
2037-12-31