title: Preparation and rearrangement of N-vinyl nitrones: synthesis of spiroisoxazolines and fluorene-tethered isoxazoles.
abstract: N-Vinyl nitrones derived from fluorenone have been prepared via a copper-mediated coupling between fluorenone oxime and vinyl boronic acids. These compounds undergo subsequent rearrangement and addition reactions that are distinct from the traditional [3 + 2] cycloaddition reactivity of nitrones. Thermal rearrangements of fluorenone N-vinyl nitrones give spiroisoxazolines, while treatment with alkynes provides fluorene-tethered isoxazoles. The scope and limitations of the preparation of fluorenone N-vinyl nitrones and their subsequent rearrangement and addition reactions are discussed.
authors.affiliation: University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.
authors.forename: Dong-Liang
authors.initials: DL
authors.lastname: Mo
authors.forename: Donald A
authors.initials: DA
authors.lastname: Wink
authors.forename: Laura L
authors.initials: LL
authors.lastname: Anderson