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Full-Text Articles in Physical Sciences and Mathematics
Synthesis, Crystal Structure, And Rearrangements Of Ortho-Cyclophane Cyclotetraveratrylene (Cttv) Tetraketone, Marlon R. Lutz Jr., Matthias Zeller, Samuel R.S. Sarsah, Artur Filipowicz, Hailey Wouters, Daniel Becker
Synthesis, Crystal Structure, And Rearrangements Of Ortho-Cyclophane Cyclotetraveratrylene (Cttv) Tetraketone, Marlon R. Lutz Jr., Matthias Zeller, Samuel R.S. Sarsah, Artur Filipowicz, Hailey Wouters, Daniel Becker
Daniel P. Becker
Oxidation of cyclotetraveratrylene (CTTV) with potassium permanganate in pyridine under reflux gave tetraketone (the [14]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 …