Beckmann Rearrangement of Cyclotriveratrylene (CTV) Oxime: Tandem Beckmann-Electrophilic Aromatic Addition

Marlon R. Lutz; Matthias Zeller; Daniel P. Becker

doi:10.1016/j.tetlet.2008.06.056

Beckmann Rearrangement of Cyclotriveratrylene (CTV) Oxime: Tandem Beckmann-Electrophilic Aromatic Addition

Marlon R. Lutz, Matthias Zeller, Daniel P. Becker

Department of Chemistry and Biochemistry

Loyola University Chicago

Research output: Contribution to journal › Article › peer-review

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.

Original language	American English
Journal	Chemistry: Faculty Publications and Other Works
Volume	49
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2008.06.056
State	Published - Aug 18 2008

Keywords

Beckmann rearrangement
cyclotriveratrylene oxime

Disciplines

Chemistry

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Beckmann Rearrangement of Cyclotriveratrylene (CTV) Oxime TandemFinal published version, 199 KBLicense: Unspecified

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title = "Beckmann Rearrangement of Cyclotriveratrylene (CTV) Oxime: Tandem Beckmann-Electrophilic Aromatic Addition",

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.",

keywords = "Beckmann rearrangement, cyclotriveratrylene oxime",

author = "Lutz, {Marlon R.} and Matthias Zeller and Becker, {Daniel P.}",

year = "2008",

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journal = "Chemistry: Faculty Publications and Other Works",

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AU - Lutz, Marlon R.

AU - Zeller, Matthias

AU - Becker, Daniel P.

PY - 2008/8/18

Y1 - 2008/8/18

N2 - 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.

AB - 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.

KW - Beckmann rearrangement

KW - cyclotriveratrylene oxime

UR - https://ecommons.luc.edu/chemistry_facpubs/27

U2 - 10.1016/j.tetlet.2008.06.056

DO - 10.1016/j.tetlet.2008.06.056

M3 - Article

VL - 49

JO - Chemistry: Faculty Publications and Other Works

JF - Chemistry: Faculty Publications and Other Works

IS - 34

ER -

Beckmann Rearrangement of Cyclotriveratrylene (CTV) Oxime: Tandem Beckmann-Electrophilic Aromatic Addition

Abstract

Keywords

Disciplines

Access to Document

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