Photoinduced electron transfer from dialkyl nitroxides to halogenated solvents

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DOIResolve DOI: http://doi.org/10.1021/jo00290a046
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TypeArticle
Journal titleJournal of Organic Chemistry
ISSN0022-3263
Volume55
Issue3
Pages10611065; # of pages: 5
AbstractLaser flash photolysis (LFP) at wavelengths within the charge-transfer absorption present in CCl 4 solutions of 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) yields the oxoammonium chloride of TEMPO, 1 (λ max = 460 nm), and the trichloromethyl radical in an essentially instantaneous (≤18 ps) process. The primary photochemical event is an electron transfer from TEMPO to CCl 4, and this is followed by immediate decomposition of the CCl 4 •- radical anion to Cl - and Cl 3C •. An independent synthesis of 1 confirmed that the absorption attributed to this species had been correctly assigned. The formation of Cl 3C • was inferred by its trapping by molecular oxygen. LFP of TEMPO in other halogenated solvents and of other nitroxides in halogenated solvents has confirmed the generality of these photoreactions. Published 1990 by the American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276673
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Record identifierb3a8f3bd-ac26-4e20-a60a-9b46d107a54c
Record created2015-10-13
Record modified2016-05-09
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