title: An unexpected 2,3-dihydrofuran derivative ring opening initiated by electrophilic bromination: scope and mechanistic study.
abstract: An unexpected 2,3-dihydrofuran ring opening process at the C(4)-C(5) bond has been developed. N-Bromosuccinimide and DABCO were used as the electrophilic halogen source and the catalyst, respectively. Mechanistic study indicates that moisture in the solvent might contribute to the reaction. The resulting brominated product could be further oxidized to yield a synthetically valuable 1,2-diketo building block.
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
authors.forename: Yi
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
authors.forename: Ying-Chieh
authors.initials: YC
authors.lastname: Wong
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
authors.forename: Ying-Yeung
authors.initials: YY
authors.lastname: Yeung
mesh_terms: D001974:Bromosuccinimide / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry*
chemical_list: D005663:Furans; D007659:Ketones; D010879:Piperazines; C073812:2,3-dihydrofuran; D001974:Bromosuccinimide; C007306:triethylenediamine