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

Date

2007

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

Keywords

Keywords: adamantane derivative; methane; organohalogen derivative; trimethylsilyl derivative; tris(trimethylsilyl)methane; unclassified drug; article; chemical bond; chemical reaction kinetics; dehalogenation; mathematical analysis; reaction analysis; reduction; t Ab initio calculations; Radicals; Synthetic methods

Citation

Source

Tetrahedron Letters

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

Restricted until

2037-12-31