title: Six- versus five-membered ring formation in radical cyclizations of 7-bromo-substituted hexahydroindolinones.
abstract: [reaction: see text] Radical cyclization of N-allyl-7-bromo-3a-methyl-hexahydroindol-2-one affords a six-membered ring product that prevails over the isomeric five-membered compound. The former product is generated through two reaction pathways: (a) 6-endo-trig ring closure and (b) rearrangement of an intermediate methylenecyclopentyl radical obtained by 5-exo-trig cyclization.
authors.affiliation: Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
authors.forename: Paitoon
authors.initials: P
authors.lastname: Rashatasakhon
authors.forename: Ayse Daut
authors.initials: AD
authors.lastname: Ozdemir
authors.forename: Jerremey
authors.initials: J
authors.lastname: Willis
authors.forename: Albert
authors.initials: A
authors.lastname: Padwa