Facile synthesis of tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones from phenols with an olefin bearing an electron-attracting group at the side chain

Shojiro Maki, Seiji Kosemura, Shosuke Yamamura, Shigeru Ohba

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

3,4-Dimethoxyphenol with a trans p-nitrostyryl group at the side chain was electrolyzed in acetic anhydride containing nBu4NBF4 to afford a tricyclo[5.3.1.01,5]undec-9-ene-8,11-dione, while the cis isomer was converted into a tricyclo[5.4.0.01,5]undec-9-ene-8,11-dione as a major product. In the case of several phenols with an α,β-unsaturated ketone or ester grouping, the corresponding tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones were also obtained in good yields.

Original languageEnglish
Pages (from-to)6083-6086
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number38
DOIs
Publication statusPublished - 1993 Sep 17

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Bearings (structural)
Phenols
Alkenes
Ketones
Isomers
Esters
Electrons
acetic anhydride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Facile synthesis of tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones from phenols with an olefin bearing an electron-attracting group at the side chain. / Maki, Shojiro; Kosemura, Seiji; Yamamura, Shosuke; Ohba, Shigeru.

In: Tetrahedron Letters, Vol. 34, No. 38, 17.09.1993, p. 6083-6086.

Research output: Contribution to journalArticle

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abstract = "3,4-Dimethoxyphenol with a trans p-nitrostyryl group at the side chain was electrolyzed in acetic anhydride containing nBu4NBF4 to afford a tricyclo[5.3.1.01,5]undec-9-ene-8,11-dione, while the cis isomer was converted into a tricyclo[5.4.0.01,5]undec-9-ene-8,11-dione as a major product. In the case of several phenols with an α,β-unsaturated ketone or ester grouping, the corresponding tricyclo[5.4.0.01,5]undec-9-ene-8,11-diones were also obtained in good yields.",
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