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Synlett 2005(6): 0947-0950  
DOI: 10.1055/s-2005-864805
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2(5H)-Furanones via Oxidative Ring Expansion of 4-Hydroxy-2-cyclobutenones

Guido Verniest, Norbert De Kimpe*
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Gent, Belgium
Fax: +32(9)2646243; e-Mail: norbert.dekimpe@UGent.be;
Further Information

Publication History

Received 26 January 2005
Publication Date:
23 March 2005 (online)

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Abstract

A new method to reduce cyclobutenediones towards 4-hydroxy-2-cyclobutenones was established. The latter compounds gave rise to new 5-halo-2(5H)-furanones by reaction with halogenating agents via a cationic ring-opening-ring-closure mechanism.

Key words

cyclobutenones - 2(5H)-furanones - ring expansion - rearrangements - oxidations

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