Article
Isolation of the Saddle and Crown Conformers of Cyclotriveratrylene (CTV) Oxime
Tetrahedron Letters
Document Type
Article
Publication Date
9-3-2007
Pages
6368-6371
Publisher Name
Elsevier
Disciplines
Abstract
The oxime of cyclotriveratrylene (CTV) has been prepared and the individual crown and saddle conformers were isolated and characterized. The equilibrium constant was measured in CDCl3 and in DMSO-d6 and was shown to favor the crown conformer by an order of magnitude in DMSO-d6, relative to an approximately equal mixture at equilibrium in CDCl3. The time course for interconversion of the saddle to the crown was measured by 1H NMR and the t1/2 of the saddle was determined to be 2.45 h in CDCl3 at 25 °C, and 3.71 h in DMSO-d6.
Creative Commons License
Creative Commons Attribution-Noncommercial-No Derivative Works 3.0
Copyright Statement
© 2007 Elsevier
Citation Information
Marlon R. Lutz, David C. French, Peter Rehage and Daniel P. Becker. "Isolation of the Saddle and Crown Conformers of Cyclotriveratrylene (CTV) Oxime" Tetrahedron Letters Vol. 48 Iss. 36 (2007) Available at: http://works.bepress.com/daniel_p_becker/96/
Author Posting © Elsevier, 2007. This is the author's version of the work. It is posted here by permission of Elsevier for personal use, not for redistribution. The definitive version was published in Tetrahedron Letters, Volume 48, Issue 36, September 3, 2007. http://dx.doi.org/10.1016/j.tetlet.2007.07.004