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

Tools

Jones, D. Heulyn and Bresciani, Stefano and Tellam, James P. and Wojno, Justyna and Cooper, Anthony W J and 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. ISSN 1477-0520 (https://doi.org/10.1039/c5ob01924a)

[thumbnail of Jones-etal-OBC2016-synthesis-dibenzylamino-1-methylcyclohexanol]
Preview
 Text. Filename: Jones_etal_OBC2016_synthesis_dibenzylamino_1_methylcyclohexanol.pdf
Accepted Author Manuscript
Download (842kB)| Preview

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.

ORCID iDs

Jones, D. Heulyn, Bresciani, Stefano, Tellam, James P., Wojno, Justyna, Cooper, Anthony W J, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Tomkinson, Nicholas C O ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
  • Item type:Article
    ID code:55978
    Dates:
    Date
    Event
    1 January 2016
    Published
    8 October 2015
    Published Online
    8 October 2015
    Accepted
    Subjects:Science > Chemistry
    Department:UNSPECIFIED
    Depositing user: Pure Administrator
    Date deposited:22 Mar 2016 12:36
    Last modified:11 Nov 2024 11:18
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/55978
CORE (COnnecting REpositories)