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

Guido Verniest; Norbert De Kimpe

doi:10.1055/s-2005-864805

LETTER

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;

Abstract

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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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References

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