title: Isoxazole to oxazole: a mild and unexpected transformation.
abstract: 3-Aryltetrahydrobenzisoxazoles prepared en route to the coleophomone natural products and analogues, were found to undergo a remarkable base-mediated rearrangement to 2-aryltetrahydrobenzoxazoles. The scope of this unprecedented, facile transformation was probed: a range of analogues was produced, a mechanism proposed, and an application demonstrated by synthesis of a known herbicidal compound.
authors.affiliation: Department of Chemistry, Loughborough University, Leics. LE11 3TU, UK. r.c.f.jones@lboro.ac.uk.
authors.forename: Raymond C F
authors.initials: RC
authors.lastname: Jones
authors.forename: Alexander
authors.initials: A
authors.lastname: Chatterley
authors.forename: Romain
authors.initials: R
authors.lastname: Marty
authors.forename: W Martin
authors.initials: WM
authors.lastname: Owton
authors.forename: Mark R J
authors.initials: MR
authors.lastname: Elsegood
mesh_terms: D018360:Crystallography, X-Ray; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D007555:Isoxazoles; D010080:Oxazoles; C469250:coleophomone C