Reactions of bicyclic nitroxides involving reduction of the NO group

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DOIResolve DOI: http://doi.org/10.1021/ja00800a039
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TypeArticle
Journal titleJournal of the American Chemical Society
ISSN0002-7863
Volume95
Issue19
Pages63956400; # of pages: 6
AbstractThe preparation of nortropane N-oxyl (8-azabicyclo[3.2. 1]octane N-oxyl) and some homologs and derivatives is described. This radical oxidizes hydrogen peroxide and 2-propanol; labeling studies show that the bridgehead protons are not involved in these reactions. Nortropane N-oxyl dimerizes irreversibly in several solvents to give a product resulting from attack at a bridgehead position. In benzene at temperatures from 10 to 65°, the rate of this reaction is described by the equation kdec = 1010.9 exp(-21,700 plusmn; 1800 cal/RT) M-1 sec-1. The homolog, 9-azabicyclo[3.3.1]nonane N-oxyl, decays very much more slowly. In benzene at 30° this decay appears to be a first- rather than a second-order process.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276715
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Record identifier42114d6e-5d19-4f18-ac33-04801b6d3cc9
Record created2015-10-13
Record modified2016-05-09
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