TY - JOUR
T1 - 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
AU - Maki, Shojiro
AU - Kosemura, Seiji
AU - Yamamura, Shosuke
AU - Ohba, Shigeru
N1 - Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.
PY - 1993/9/17
Y1 - 1993/9/17
N2 - 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.
AB - 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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U2 - 10.1016/S0040-4039(00)61734-3
DO - 10.1016/S0040-4039(00)61734-3
M3 - Article
AN - SCOPUS:0027451960
VL - 34
SP - 6083
EP - 6086
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 38
ER -