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Communication | Regular issue | Vol 78, No. 6, 2009, pp.1427-1432
Published online, 6th February, 2009
DOI: 10.3987/COM-09-11640
Novel Application of an Electrooxidative Method for the Formation of a Tetrahydrofuran Ring from 5-Hydroxy-2-pentanone Phenylhydrazone

Mitsuhiro Okimoto,* Takashi Yoshida, Masayuki Hoshi, Kazuyuki Hattori, Masashi Komata, and Tomohito Chiba

*Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology, Koen-cho 165, Kitami, Hokkaido 090-8507, Japan

Abstract

Various ketone phenylhydrazones that possess a hydroxy group on the parent ketone moiety were subjected to electrooxidation in methanol in the presence of KI and NaOMe. In the case of 4-hydroxy-2-butanone phenylhydrazone, the nucleophilic attack of the azomethine carbon by a methoxide ion affording the corresponding methoxy(phenylazo)alcohol was dominant. Interestingly, however, in the case of 5-hydroxy-2-pentanone phenylhydrazone, similar reaction conditions favored the intramolecular cyclization to afford a (phenylazo)tetrahydrofuran derivative.