Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers

D. Heulyn Jones, Stefano Bresciani, James P. Tellam, Justyna Wojno, Anthony W J Cooper, Alan R. Kennedy, Nicholas C O Tomkinson

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The isomers of dibenzylamino-1-methylcyclohexan-1-ol and dibenzylamino-1-trifluoromethylcyclohexan-1-ol have been prepared. The stereochemistry of these compounds was unequivocally assigned through a combination of NMR spectroscopy and single crystal X-ray analysis. The cis-isomer of 3-N,N-dibenzylamino-1-trifluoromethylcyclohexanol and its derivatives display an unusual conformational behaviour in both solution-phase and the solid-state, where the amino group usually adopts an axial conformation.

LanguageEnglish
Pages172-182
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number1
Early online date8 Oct 2015
DOIs
Publication statusPublished - 1 Jan 2016

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Isomers
Magnetic Resonance Spectroscopy
isomers
X-Rays
Stereochemistry
X ray analysis
stereochemistry
synthesis
Nuclear magnetic resonance spectroscopy
Conformations
Single crystals
Derivatives
solid state
nuclear magnetic resonance
single crystals
spectroscopy
crystals
x rays
dibenzylamino-1-trifluoromethylcyclohexanol
dibenzylamino-1-methylcyclohexanol

Keywords

  • NMR Spectroscopy
  • single crystal X-ray analysis
  • dibenzylamino-1-methylcyclohexan-1-ol
  • dibenzylamino-1-trifluoromethylcyclohexan-1-ol

Cite this

Jones, D. Heulyn ; Bresciani, Stefano ; Tellam, James P. ; Wojno, Justyna ; Cooper, Anthony W J ; Kennedy, Alan R. ; Tomkinson, Nicholas C O. / Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers. In: Organic and Biomolecular Chemistry. 2016 ; Vol. 14, No. 1. pp. 172-182.
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abstract = "The isomers of dibenzylamino-1-methylcyclohexan-1-ol and dibenzylamino-1-trifluoromethylcyclohexan-1-ol have been prepared. The stereochemistry of these compounds was unequivocally assigned through a combination of NMR spectroscopy and single crystal X-ray analysis. The cis-isomer of 3-N,N-dibenzylamino-1-trifluoromethylcyclohexanol and its derivatives display an unusual conformational behaviour in both solution-phase and the solid-state, where the amino group usually adopts an axial conformation.",
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Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers. / Jones, D. Heulyn; Bresciani, Stefano; Tellam, James P.; Wojno, Justyna; Cooper, Anthony W J; Kennedy, Alan R.; Tomkinson, Nicholas C O.

In: Organic and Biomolecular Chemistry, Vol. 14, No. 1, 01.01.2016, p. 172-182.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Jones, D. Heulyn

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AU - Tellam, James P.

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AU - Cooper, Anthony W J

AU - Kennedy, Alan R.

AU - Tomkinson, Nicholas C O

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AB - The isomers of dibenzylamino-1-methylcyclohexan-1-ol and dibenzylamino-1-trifluoromethylcyclohexan-1-ol have been prepared. The stereochemistry of these compounds was unequivocally assigned through a combination of NMR spectroscopy and single crystal X-ray analysis. The cis-isomer of 3-N,N-dibenzylamino-1-trifluoromethylcyclohexanol and its derivatives display an unusual conformational behaviour in both solution-phase and the solid-state, where the amino group usually adopts an axial conformation.

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