Cyclooctatetraenoquinones. I The synthesis and structure of dibenzo[a,e]cyclooctene-5,6-dione

Abstract
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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