title: Reaction of azides with dichloroindium hydride: very mild production of amines and pyrrolidin-2-imines through possible indium-aminyl radicals.
abstract: Organic azides are easily reduced to the corresponding amines by reaction with dichloroindium hydride under very mild conditions and in a highly chemoselective fashion. Gamma-azidonitriles give rise to outstanding five-membered cyclizations affording pyrrolidin-2-imines. A rationalization of the overall experimental data cannot exclude the occurrence of competitive radical and nonradical pathways, but certain results are, however, soundly consistent with the intermediacy of indium-bound nitrogen-centered radicals. [reaction: see text]
authors.affiliation: Dipartimento di Chimica Organica A. Mangini, Università di Bologna, Viale Risorgimento 4, I-40136 Bologna, Italy.
authors.forename: Luisa
authors.initials: L
authors.lastname: Benati
authors.forename: Giorgio
authors.initials: G
authors.lastname: Bencivenni
authors.forename: Rino
authors.initials: R
authors.lastname: Leardini
authors.forename: Daniele
authors.initials: D
authors.lastname: Nanni
authors.forename: Matteo
authors.initials: M
authors.lastname: Minozzi
authors.forename: Piero
authors.initials: P
authors.lastname: Spagnolo
authors.forename: Rosanna
authors.initials: R
authors.lastname: Scialpi
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Zanardi