Isolation of the Saddle and Crown Conformers of Cyclotriveratrylene (CTV) Oxime

Marlon R. Lutz; David C. French; Peter Rehage; Daniel P. Becker

doi:10.1016/j.tetlet.2007.07.004

Isolation of the Saddle and Crown Conformers of Cyclotriveratrylene (CTV) Oxime

Marlon R. Lutz, David C. French, Peter Rehage, Daniel P. Becker

Department of Chemistry and Biochemistry

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

Abstract

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.

Original language	American English
Journal	Chemistry: Faculty Publications and Other Works
Volume	48
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2007.07.004
State	Published - Sep 3 2007

Keywords

cyclotriveratrylene oxime

Disciplines

Chemistry

Access to Document

10.1016/j.tetlet.2007.07.004License: Unspecified

Isolation of the Saddle and Crown Conformers of CyclotriveratryleFinal published version, 499 KBLicense: Unspecified

Cite this

@article{ff1dc87d4e6f4b0cb155f77cc93f5ccd,

title = "Isolation of the Saddle and Crown Conformers of Cyclotriveratrylene (CTV) Oxime",

abstract = " 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.",

keywords = "cyclotriveratrylene oxime",

author = "Lutz, \{Marlon R.\} and French, \{David C.\} and Peter Rehage and Becker, \{Daniel P.\}",

year = "2007",

month = sep,

day = "3",

doi = "10.1016/j.tetlet.2007.07.004",

language = "American English",

volume = "48",

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

number = "36",

}

TY - JOUR

T1 - Isolation of the Saddle and Crown Conformers of Cyclotriveratrylene (CTV) Oxime

AU - Lutz, Marlon R.

AU - French, David C.

AU - Rehage, Peter

AU - Becker, Daniel P.

PY - 2007/9/3

Y1 - 2007/9/3

N2 - 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.

AB - 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.

KW - cyclotriveratrylene oxime

UR - https://ecommons.luc.edu/chemistry_facpubs/25

U2 - 10.1016/j.tetlet.2007.07.004

DO - 10.1016/j.tetlet.2007.07.004

M3 - Article

VL - 48

JO - Chemistry: Faculty Publications and Other Works

JF - Chemistry: Faculty Publications and Other Works

IS - 36

ER -

Isolation of the Saddle and Crown Conformers of Cyclotriveratrylene (CTV) Oxime

Abstract

Keywords

Disciplines

Access to Document

Other files and links

Cite this