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Synthesis and Crystal Structures of 2-Azido-4-aminocyclohexane-1,3-diols

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Abstract

2-Azido-4-aminocyclohexane-1,3-diols 12, 14 and 16 were synthesised and their crystal structures were studied by X-ray diffraction. Compound 12 crystallizes in the monoclinic space group P2 1 /n with cell parameters of a = 13.7059(2) Å, b = 10.8861(2) Å, c = 13.8675(3) Å, β = 117.2365(10)°, V = 1839.67(6) Å3 and Z = 4. Compound 14 crystallizes in the orthorhombic space group Pcab with cell parameters of a = 9.9508(1) Å, b = 10.9839(2) Å, c = 24.7035(4) Å, V = 2700.06(7) Å3 and Z = 8. Compound 16 crystallizes in the triclinic space group \(\text{P}\bar{\it{1}}\) with cell parameters of a = 10.9511(3) Å, b = 11.3148(3) Å, c = 15.9545(5) Å, α = 86.3487(11)°, β = 87.4723(11)°, γ = 89.3398(10)°, V = 1970.91(10) Å3 and Z = 4. All three structures were characterised by arrays of hydrogen bonding interactions and these crystallographic studies also revealed their conformations, which gave valuable information into the regioselectivity of epoxide ring-opening during their formation.

Graphical Abstract

Three 2-azido-4-aminocyclohexane-1,3-diols 12, 14 and 16 were synthesised and their crystal structures were studied by X-ray diffraction. All three structures were characterised by arrays of hydrogen bonding interactions and these crystallographic studies also revealed valuable conformational data which was used to rationalise the regioselectivity of epoxide ring-opening during their formation.

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Notes

  1. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 1021309 (2), 1028347 (3), 1028344 (8) and 1028345 (9); see [17, 20].

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Acknowledgments

The authors would like to thank the National University of Ireland for a travelling studentship (M.B.B.).

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Authors and Affiliations

  1. Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK

    Méabh B. Brennan, Stephen G. Davies, James A. Lee, Amber L. Thompson & James E. Thomson

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  1. Méabh B. Brennan
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  2. Stephen G. Davies
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  4. Amber L. Thompson
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  5. James E. Thomson
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Correspondence to Stephen G. Davies.

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Brennan, M.B., Davies, S.G., Lee, J.A. et al. Synthesis and Crystal Structures of 2-Azido-4-aminocyclohexane-1,3-diols. J Chem Crystallogr 45, 401–409 (2015). https://doi.org/10.1007/s10870-015-0607-x

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  • DOI: https://doi.org/10.1007/s10870-015-0607-x

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