5-endo closure of the 2-formylbenzoyl radical

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DOIResolve DOI: http://doi.org/10.1021/ja00084a012
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TypeArticle
Journal titleJournal of the American Chemical Society
ISSN0002-7863
Volume116
Issue5
Pages17181724; # of pages: 7
AbstractThe 5-endo cyclization of the 2-formylbenzoyl radical (reaction 2) is shown to be a highly favored process relative to the alternative, 4-exo-trig ring closure. This evidence comes from product studies, including ESR and laser flash photolysis studies of transient radical intermediates, from a nitroxide trapping measurement of the rate constant for cyclization of the 2-formylbenzoyl radical, viz., k 2 = 2 × 10 8 s -1 at 45 °C, and from the estimated favorable enthalpic change for 5-endo cyclization vs 4-exo-trig cyclization. It is suggested that rotation of the formyl group in the initially formed conformer of the 2-formylbenzoyl radical may be the rate limiting step in this cyclization.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC)
Peer reviewedYes
NPARC number21276794
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Record identifierc09c14be-0299-4e8d-9f8b-e374fa8d8e23
Record created2015-10-13
Record modified2016-05-09
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