Journal
ORGANIC LETTERS
Volume 7, Issue 1, Pages 155-158Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol047716+
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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,beta-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.
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