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

From National Research Council Canada

DOIResolve DOI: https://doi.org/10.1021/ol047716+
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Affiliation
  1. National Research Council of Canada. National Institute for Nanotechnology
FormatText, Article
Abstract
Carbamoyl 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
In
  • Organic Letters 7, no. 1 (6 January 2005): 155–158.
LanguageEnglish
Peer reviewedYes
NRC number70
NPARC number12327905
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Record identifier9e93e508-d366-49cb-a165-eeff1db67cce
Record created2009-09-10
Record modified2020-04-07
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