A carbon-centered radical unreactive toward oxygen: Unusual radical stabilization by a lactone ring

DOI	Trouver le DOI : https://doi.org/10.1021/ol9913946
Auteur	Rechercher : Scaiano, J.C.; Rechercher : Martin, A.; Rechercher : Yap, G.P.A.; Rechercher : Ingold, K. U.¹
Affiliation	Conseil national de recherches du Canada
Format	Texte, Article
Résumé	(equation presented) A lactone ring confers unusual stability to a diphenylmethyl-like radical that is virtually unreactive toward oxygen. Thus, the radical derived from HP-136 is about 10 000 times less reactive than typical carbon-centered radicals. A reversible reaction with oxygen is proposed by analogy with triphenylmethyl; however, the association constant is about 1000 times smaller for HP-136 than for triphenylmethyl. While the lactone ring greatly influences the reactivity, the spectroscopy of the HP-136-derived radical is in line with that expected for a substituted diphenylmethyl radical.
Date de publication	2000
Dans	Organic Letters 2, nº 7 (2000) : 899–901.
Langue	anglais
Publications évaluées par des pairs	Oui
Numéro NPARC	21276631
Exporter la notice	Exporter en format RIS
Signaler une correction	Signaler une correction (s'ouvre dans un nouvel onglet)
Identificateur de l’enregistrement	12d1a166-4d2b-41ed-9032-ee5d5a39364d
Enregistrement créé	2015-10-13
Enregistrement modifié	2020-03-26