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

DOI	Trouver le DOI : https://doi.org/10.1021/ol047716+
Auteur	Rechercher : DiLabio, Gino A.¹; Rechercher : Scanlan, Eoin M.; Rechercher : Walton, John C.
Affiliation	Conseil national de recherches du Canada. Institut national de nanotechnologie
Format	Texte, Article
Résumé	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.
Date de publication	2005-01-06
Dans	Organic Letters 7, nº 1 (6 janvier 2005) : 155–158.
Langue	anglais
Publications évaluées par des pairs	Oui
Numéro du CNRC	70
Numéro NPARC	12327905
Exporter la notice	Exporter en format RIS
Signaler une correction	Signaler une correction (s'ouvre dans un nouvel onglet)
Identificateur de l’enregistrement	9e93e508-d366-49cb-a165-eeff1db67cce
Enregistrement créé	2009-09-10
Enregistrement modifié	2020-04-07