title: Fluorinated heterocyclic compounds. An expedient route to 5-perfluoroalkyl-1,2,4-triazoles via an unusual hydrazinolysis of 5-perfluoroalkyl-1,2,4-oxadiazoles: first examples of an ANRORC-like reaction in 1,2,4-oxadiazole derivatives.
abstract: The hydrazinolysis reaction of 5-perfluoroalkyl-1,2,4-oxadiazoles has been investigated. Nucleophilic addition of the reagent to the C(5)-N(4) double bond of the oxadiazole ring, followed by ring-opening and then ring-closure involving the beta-nitrogen atom of the hydrazino moiety and the C(3) of the oxadiazole ring, explains the formation of 5-perfluoroalkyl-1,2,4-triazoles as final products. Useful applications in synthesis of this uncommon hydrazinolysis can be claimed.
authors.affiliation: Dipartimento di Chimica Organica A. Mangini, Università degli Studi di Bologna, Via S. Donato 15, Italy.
authors.forename: Silvestre
authors.initials: S
authors.lastname: Buscemi
authors.forename: Andrea
authors.initials: A
authors.lastname: Pace
authors.forename: Ivana
authors.initials: I
authors.lastname: Pibiri
authors.forename: Nicolò
authors.initials: N
authors.lastname: Vivona
authors.forename: Domenico
authors.initials: D
authors.lastname: Spinelli