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Synlett 1998; 1998(6): 599-600
DOI: 10.1055/s-1998-1752
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Synthesis of 5-Substituted 4,4-Disubstituted 2-Cyclohexen-1-ones by Electro-Generated Base Promoted Michael Addition of 4,4-Disubstituted 2,5-Cyclohexadien-1-ones

Sigeru Torii* , Naoya Hayashi, Manabu Kuroboshi
  • *Dept. of Applied Chem., Faculty of Engin., Okayama University, Tsushima-naka 3-1-1, Okayama 700, Japan; Fax + 81(86)2 55 34 24; E-mail: toriiken@cc.okayama-u.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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5-Substituted 4,4-dialkoxy-2-cyclohexen-1-ones were electrosynthesized from 4,4-disubstituted 2,5-cyclohexadien-1-ones, which were obtained from 1,4-dialkoxybenzene derivatives by electrolysis, by electro-generated base (EG-base)-promoted Michael addition with CH2E2 (E = CO2R, COMe) in moderate to almost quantitative yield. The cyclohexenone derivatives were found to be a good precursor of benzofuranone derivatives through acid-promoted intramolecular lactonization.

EG-base - Michael addition - 5-substituted 4,4-disubstituted 2-cyclohexen-1-one - benzofuranone - lactonization

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