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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. and Tomkinson, Nicholas C. O. 2016. Synthesis of dibenzylamino-1-methylcyclohexanol and dibenzylamino-1-trifluoromethylcyclohexanol isomers. Organic and Biomolecular Chemistry 14 (1) , pp. 172-182. 10.1039/C5OB01924A

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Biosciences
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Date of Acceptance: 8 October 2015
Last Modified: 10 Jun 2020 11:30

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