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The axial substituent is typically more shielded as compared to the equatorial one as indicated by the chemical shifts of H-2ax and H-2eq in this report. Similar results regarding the chemical shifts of methyl group on methylcyclohexane can be found in the literature as well Wiberg, K. B, Hammer, J. D, Castejon, H, Bailey, W. F, DeLeon, E. L, Jarret, R. M. J. Org. Chem. 1999, 64, 2085-2095, However, computational analysis of the electron density and electrostatic potential for the axial and equatorial azido groups on cyclohexane reveals only slight difference favoring equatorial azido group toward nucleophilic agent. Thus, we reason that a combination of stereoelectronic effect and steric hindrance should contribute to the lower reactivity of the N-2‴ azido group
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