Studies on the spiro[2.5]octadienyl radical and the 2-phenylethyl rearrangement

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DOIResolve DOI: http://doi.org/10.1021/ja00539a015
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TypeArticle
Journal titleJournal of the American Chemical Society
ISSN0002-7863
Volume102
Issue19
Pages60636068; # of pages: 6
AbstractThe title radical, 5, has been generated by hydrogen atom abstraction from spiro[2.5]octa-4,6-diene (4). The radical could not be observed by EPR spectroscopy even at temperatures as low as 100 K. Instead, the EPR spectrum of the cyclopropyl ring-opened product was obtained, 2-phenylethyl (6). However, 5 was identified by using optical detection methods by means of its absorption and fluorescence at ca. 560 nm, which is a characteristic of cyclohexadienyls. The rate constant for H atom abstraction from 4 by tert-butoxyl was measured at 295 K, and approximate Arrhenius parameters for the 5 to 6 rearrangement have been estimated. The hydrocarbon 4 is remarkably resistant to the thermodynamically favored, radical induced rearrangement to ethyl benzene. © 1980 American Chemical Society.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276638
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Record identifier457e5374-7fcd-49a1-b416-96b6c81f7e47
Record created2015-10-13
Record modified2016-05-09
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