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Review | Regular issue | Vol 63, No. 11, 2004, pp.2627-2648
Published online, 10th August, 2004
DOI: 10.3987/REV-04-584
Molecular Rearrangements of 1-Oxa-2-azoles as an Expedient Route to Fluorinated Heterocyclic Compounds

Andrea Pace, Ivana Pibiri, Silvestre Buscemi, and Nicolò Vivona*

*Dipartimento di Chimica Organica “E. Paternò”, Università degli Studi di Palermo, Viale delle Scienze-Parco d’Orleans II, 90128 Palermo, Italy


Molecular rearrangements of O-N bond-containing azoles (1-oxa-2-azoles) represent a wide class of reactions by which various heterocycle-to-heterocycle transformations can be performed as alternative synthetic methodologies. The material presented in this review is an extensive survey of both thermal and photochemical methodologies that have been applied to fluorinated oxadiazoles, and shows how molecular rearrangements can be an alternative and in some cases the most convenient route for the synthesis of several fluorinated heterocycles.