Article
Beckmann Rearrangement of Cyclotriveratrylene (CTV) Oxime: Tandem Beckmann-Electrophilic Aromatic Addition
Tetrahedron Letters
Document Type
Article
Publication Date
8-18-2008
Pages
5003-5005
Publisher Name
Elsevier
Disciplines
Abstract
The Beckmann rearrangement has been performed on the oxime of cyclotriveratrylene (CTV) with thionyl chloride affording the ring-expanded 10-membered ring amide exclusively in high yield. Modified conditions afford a helical pentacycle derived from an unusual tandem Beckmann rearrangement and electrophilic aromatic addition followed by demethylation and tautomerization.
Creative Commons License
Creative Commons Attribution-Noncommercial-No Derivative Works 3.0
Copyright Statement
© 2008 Elsevier
Citation Information
Marlon R. Lutz, Matthias Zeller and Daniel P. Becker. "Beckmann Rearrangement of Cyclotriveratrylene (CTV) Oxime: Tandem Beckmann-Electrophilic Aromatic Addition" Tetrahedron Letters Vol. 49 Iss. 34 (2008) Available at: http://works.bepress.com/daniel_p_becker/94/
Author Posting © Elsevier, 2008. 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 49, Issue 34, August 18, 2008. http://dx.doi.org/10.1016/j.tetlet.2008.06.056