Taylor & Francis
Oxidation of cyclotetraveratrylene (CTTV) with potassium permanganate in pyridine under reflux gave tetraketone (the ketonand) 3 which exists as a previously unobserved barrel conformation with S4symmetry in the crystal structure, although the more familiar ‘boat’ conformer was shown by semi-empirical AM1 calculations to be 3.03 kcal/mol lower in energy. In addition to CTTV tetraketone 3, an isomeric bis-spirolactone 4 was isolated from the basic oxidation conditions, analogous to the product of trans-annular attack and rearrangement observed with oxidation of cyclotriveratrylene, whereas in acid at elevated temperatures, tetraketone 3 underwent a very efficient rearrangement and decarboxylation to afford the highly symmetric spirobi[anthracene]-10,10′-dione derivative 5.
Lutz, Marlon R. Jr.; Zeller, Matthias; Sarsah, Samuel R.S.; Filipowicz, Artur; Wouters, Hailey; and Becker, Daniel. Synthesis, Crystal Structure, and Rearrangements of ortho-Cyclophane Cyclotetraveratrylene (CTTV) tetraketone. Supramolecular Chemistry, 24, 11: , 2012. Retrieved from Loyola eCommons, Chemistry: Faculty Publications and Other Works, http://dx.doi.org/10.1080/10610278.2012.719081
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