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Issue 1, 2016
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Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers

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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.

Graphical abstract: Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers

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Publication details

The article was received on 16 Sep 2015, accepted on 08 Oct 2015 and first published on 08 Oct 2015


Article type: Paper
DOI: 10.1039/C5OB01924A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2016,14, 172-182
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    Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers

    D. H. Jones, S. Bresciani, J. P. Tellam, J. Wojno, A. W. J. Cooper, A. R. Kennedy and N. C. O. Tomkinson, Org. Biomol. Chem., 2016, 14, 172
    DOI: 10.1039/C5OB01924A

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