Kinetic and Theoretical Study of 4-exo Ring Closures of Carbamoyl Radicals onto C=C and C=N Bonds

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DOIResolve DOI: http://doi.org/10.1021/ol047716+
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TypeArticle
Journal titleOrganic Letters
ISSN15237060
Volume7
Issue1
Pages155158; # of pages: 4
AbstractCarbamoyl radicals were generated from oxime oxalate amides, and the kinetics of their 4-exo cyclizations onto C=C and C=NO bonds, leading to -lactam-containing species, were studied by EPR spectroscopy. DFT computations with model carbamoyl radicals predicted 4-exo ring closures onto C=NO bonds to be facile, especially when tert-butyl substituents were present. The reverse ring-opening reactions were predicted to have much higher activation energies. Experimental evidence also favored slow reverse ring opening.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; National Institute for Nanotechnology
Peer reviewedYes
Identifier18697458
NRC number70
NPARC number12327905
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Record identifier9e93e508-d366-49cb-a165-eeff1db67cce
Record created2009-09-10
Record modified2016-05-09
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