Document Type

Article

Publication Date

8-13-2012

Publication Title

Supramolecular Chemistry

Volume

24

Issue

11

Publisher Name

Taylor & Francis

Abstract

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 spirobi[anthracene]-10,10′-dione derivative 5.

Comments

This is an Author's Accepted Manuscript of an article published in Supramolecular Chemistry, Volume 24, Issue 11, 2012 © Taylor & Francis, available online at: http://www.tandfonline.com/10.1080/10610278.2012.719081

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Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

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