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

Longshaw, Alistair; Carland , Michael; Krenske, Elizabeth; Coote, Michelle; Sherburn, Michael

Description

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...[Show more]

dc.contributor.authorLongshaw, Alistair
dc.contributor.authorCarland , Michael
dc.contributor.authorKrenske, Elizabeth
dc.contributor.authorCoote, Michelle
dc.contributor.authorSherburn, Michael
dc.date.accessioned2015-12-07T22:55:11Z
dc.identifier.issn0040-4039
dc.identifier.urihttp://hdl.handle.net/1885/28283
dc.description.abstractThe 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.
dc.publisherElsevier
dc.sourceTetrahedron Letters
dc.subjectKeywords: 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
dc.titleTris(trimethylsilyl)methane is not an effective mediator of radical reactions
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume48
dc.date.issued2007
local.identifier.absfor030799 - Theoretical and Computational Chemistry not elsewhere classified
local.identifier.absfor030505 - Physical Organic Chemistry
local.identifier.ariespublicationu4005981xPUB57
local.type.statusPublished Version
local.contributor.affiliationLongshaw, Alistair, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationCarland , Michael , College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationKrenske, Elizabeth, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationCoote, Michelle, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationSherburn, Michael, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue32
local.bibliographicCitation.startpage5585
local.bibliographicCitation.lastpage5588
local.identifier.doi10.1016/j.tetlet.2007.06.055
dc.date.updated2015-12-07T12:53:31Z
local.identifier.scopusID2-s2.0-34447250002
CollectionsANU Research Publications

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