Cyclooctatetraenoquinones. I The synthesis and structure of dibenzo[a,e]cyclooctene-5,6-dione
Dibenzo[a,e]cyclooctene-5,6-dione ( 18 ), a derivative of 1,2-cyclooctatetraenoquinone ( 4 ), has been synthesized by selenium dioxide oxidation of dibenzo[a,e]cycloocten-5(6H)-one ( 26 ), itself obtained from the reaction of 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene ( 20 ) with dimet...
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| Veröffentlicht in: | Canadian journal of chemistry 1970-03, Vol.48 (5), p.788-795 |
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| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | Dibenzo[a,e]cyclooctene-5,6-dione (
18
), a derivative of 1,2-cyclooctatetraenoquinone (
4
), has been synthesized by selenium dioxide oxidation of dibenzo[a,e]cycloocten-5(6H)-one (
26
), itself obtained from the reaction of 5,11-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene (
20
) with dimethyl sulfoxide and collidine. Infrared and proton magnetic resonance spectroscopic studies have shown that the 8-membered ring of
18
is not aromatic. |
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| ISSN: | 0008-4042 1480-3291 |
| DOI: | 10.1139/v70-128 |