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Beckmann Rearrangement Of Cyclotriveratrylene (Ctv) Oxime: Tandem Beckmann-Electrophilic Aromatic Addition, Marlon R. Lutz Jr., Matthias Zeller, Daniel P. Becker
Beckmann Rearrangement Of Cyclotriveratrylene (Ctv) Oxime: Tandem Beckmann-Electrophilic Aromatic Addition, Marlon R. Lutz Jr., Matthias Zeller, Daniel P. Becker
Chemistry: Faculty Publications and Other Works
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.