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.
Lutz, Marlon R. Jr.; French, David C.; Rehage, Peter; and Becker, Daniel P.. Isolation of the Saddle and Crown Conformers of Cyclotriveratrylene (CTV) Oxime. Tetrahedron Letters, 48, 36: , 2007. Retrieved from Loyola eCommons, Chemistry: Faculty Publications and Other Works, http://dx.doi.org/10.1016/j.tetlet.2007.07.004
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.
© 2007 Elsevier