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 language | English |
|---|---|
| Pages (from-to) | 6083-6086 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 34 |
| Issue number | 38 |
| DOIs | |
| Publication status | Published - 1993 Sep 17 |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Maki, S., Kosemura, S., Yamamura, S., & Ohba, S. (1993). 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. Tetrahedron Letters, 34(38), 6083-6086. https://doi.org/10.1016/S0040-4039(00)61734-3