Clocking Tertiary Cyclopropylcarbinyl Radical Rearrangements

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DOIResolve DOI: http://doi.org/10.1021/jo961685h
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TypeArticle
Journal titleJournal Of Organic Chemistry
ISSN00223263
Volume62
Issue5
Pages12101214; # of pages: 5
AbstractThree independent methods have been employed to estimate the rate constant, k1, for ring-opening of the 2-cyclopropyl-2-propyl radical, 1, at room temperature. These three estimates are based on chemical trapping of 1 and the ring-opened 4-methylpent-3-ene-1-yl radical by thiophenol (k1 = (1.65 ± 0.41) × 107 M-1 s-1), 9-azabicyclo[3.3.1]nonane-N-oxyl (k1 = (1.76 ± 0.34) × 107 M-1 s-1) and 2,2,6,6-tetramethylpiperidine-N-oxyl (k1 = (2.1 ± 0.4) × 107 M-1 s-1) and absolute rate constants for nonrearranging radicals structurally related to 1. The mean value for k1 ((1.84 ± 0.4) × 107 M-1 s-1) should be used when 1 is employed as a tertiary alkyl free radical clock at ambient temperatures.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier10008226
NPARC number12327846
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Record identifier9c84414b-018b-4427-bb5c-6e9a3cc3becd
Record created2009-09-10
Record modified2016-05-09
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