4.4 Article

Beckmann rearrangement of cyclotriveratrylene (CTV) oxime: tandem Beckmann-electrophilic aromatic addition

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 34, Pages 5003-5005

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.06.056

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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. (c) 2008 Elsevier Ltd, All rights reserved,

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