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

doi:10.1039/c5ob01924a

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^*

^*Corresponding author for this work

WestCHEM

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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.

Original language	English
Pages (from-to)	172-182
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	1
Early online date	8 Oct 2015
DOIs	https://doi.org/10.1039/c5ob01924a
Publication status	Published - 1 Jan 2016

Keywords

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

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10.1039/c5ob01924a

Jones-etal-OBC2016-synthesis-dibenzylamino-1-methylcyclohexanolAccepted author manuscript, 823 KB

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title = "Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers",

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.",

keywords = "NMR Spectroscopy, single crystal X-ray analysis, dibenzylamino-1-methylcyclohexan-1-ol, dibenzylamino-1-trifluoromethylcyclohexan-1-ol",

author = "Jones, \{D. Heulyn\} and Stefano Bresciani and Tellam, \{James P.\} and Justyna Wojno and Cooper, \{Anthony W J\} and Kennedy, \{Alan R.\} and Tomkinson, \{Nicholas C O\}",

year = "2016",

month = jan,

day = "1",

doi = "10.1039/c5ob01924a",

language = "English",

volume = "14",

pages = "172--182",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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T1 - Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers

AU - Jones, D. Heulyn

AU - Bresciani, Stefano

AU - Tellam, James P.

AU - Wojno, Justyna

AU - Cooper, Anthony W J

AU - Kennedy, Alan R.

AU - Tomkinson, Nicholas C O

PY - 2016/1/1

Y1 - 2016/1/1

N2 - 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.

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.

KW - NMR Spectroscopy

KW - single crystal X-ray analysis

KW - dibenzylamino-1-methylcyclohexan-1-ol

KW - dibenzylamino-1-trifluoromethylcyclohexan-1-ol

UR - https://www.scopus.com/pages/publications/84951272243

U2 - 10.1039/c5ob01924a

DO - 10.1039/c5ob01924a

M3 - Article

AN - SCOPUS:84951272243

SN - 1477-0520

VL - 14

SP - 172

EP - 182

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 1

ER -

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

Abstract

Keywords

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

Abstract

Keywords

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Data for: "Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers"

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x-ray diffractometer

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