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

Alistair I. Longshaw, Michael W. Carland, Elizabeth H. Krenske, Michelle L. Coote, Michael S. Sherburn

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5585-5588
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number32
DOIs
Publication statusPublished - 6 Aug 2007
Externally publishedYes

Keywords

  • Ab initio calculations
  • Radicals
  • Synthetic methods

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