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An Unexpected 2,3-Dihydrofuran Derivative Ring Opening Initiated by Electrophilic Bromination: Scope and Mechanistic Study

Author:
Zhao, Yi, Wong, Ying-Chieh, Yeung, Ying-Yeung
Source:
Journal of organic chemistry 2015 v.80 no.1 pp. 453-459
ISSN:
1520-6904
Subject:
Lewis acids, bromination, catalysts, chemical structure, halogens, organic chemistry, organic compounds, oxidation, solvents
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.
Agid:
5503550