Journal of Chemical Crystallography

, Volume 43, Issue 12, pp 646–654 | Cite as

Synthesis and Crystal Structures of N-Aryl-N-methylaminocyclohexanols

  • Alexander J. Cresswell
  • Stephen G. Davies
  • David S. Hewings
  • Wataru Kurosawa
  • James A. Lee
  • Melloney J. Morris
  • Paul M. Roberts
  • Amber L. Thompson
  • James E. Thomson
Original Paper

Abstract

N-Aryl-N-methylaminocyclohexanols 1012 were synthesised and their crystal structures were studied by X-ray diffraction. Compound 10 crystallizes in the monoclinic space group Cc with cell parameters of a = 13.7366(2) Å, b = 13.7234(2) Å, c = 26.9057(5) Å, β = 93.0900(5)°, V = 5064.70(14) Å3 and Z = 16. Compound 11 crystallizes in the trigonal space group \(P\bar{3}\) with cell parameters of a = b = 25.4429(4) Å, c = 9.6417(2) Å, V = 5405.27(16) Å3 and Z = 18. Compound 12 crystallizes in the monoclinic space group P21/n with cell parameters of a = 9.9511(2) Å, b = 11.5777(2) Å, c = 20.5968(4) Å, β = 95.5037(9)°, V = 2362.04(8) Å3 and Z = 8. All three structures were characterised by arrays of hydrogen bonding interactions and these crystallographic studies revealed conformations of 1012 which gave valuable information into the mechanism of the reaction during their formation.

Graphical Abstract

Crystals of (RS,RS,RS)-3-[N-methyl-N-(4'-methoxyphenyl)amino]cyclohexane-1,2-diol, (RS,RS,RS)-3-(N-methyl-N-phenylamino)cyclohexane-1,2-diol and (RS,RS,RS)-2-fluoro-6-(N-methyl-N-phenylamino)cyclohexan-1-ol were synthesised and their structures were studied by X-ray diffraction.
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Keywords

Amino alcohol Hydrogen bonding Olefinic oxidation Dihydroxylation Hydroxyfluorination 

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Alexander J. Cresswell
    • 1
  • Stephen G. Davies
    • 1
  • David S. Hewings
    • 1
  • Wataru Kurosawa
    • 1
  • James A. Lee
    • 1
  • Melloney J. Morris
    • 2
  • Paul M. Roberts
    • 1
  • Amber L. Thompson
    • 1
  • James E. Thomson
    • 1
  1. 1.Chemistry Research Laboratory, Department of ChemistryUniversity of OxfordOxfordUK
  2. 2.Syngenta, Jealott’s Hill International Research CentreBerkshireUK

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