Issue 1, 2016

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
16 Sep 2015
Accepted
08 Oct 2015
First published
08 Oct 2015

Org. Biomol. Chem., 2016,14, 172-182

Author version available

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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