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

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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 languageEnglish
Pages (from-to)172-182
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number1
Early online date8 Oct 2015
DOIs
Publication statusPublished - 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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