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American Chemical Society, Journal of Organic Chemistry, 2(68), p. 605-608, 2002

DOI: 10.1021/jo0262762

Wiley-VCH Verlag, ChemInform, 22(34), 2003

DOI: 10.1002/chin.200322123

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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

Journal article published in 2003 by Silvestre Buscemi, Andrea Pace ORCID, Ivana Pibiri, Nicolò Vivona, Domenico Spinelli
This paper is available in a repository.
This paper is available in a repository.

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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.