The difference in the bond length between axial and equatorial carbon–chlorine bonds in chlorodioxans is paralleled by a large change in the 35Cl nuclear quadrupole coupling constant and both these effects are compatible with an orientation-dependent conjugative interaction between the oxygen atom and the carbon–chlorine bond.
P. Linscheid and E. A. C. Lucken, J. Chem. Soc. D, 1970, 425b DOI: 10.1039/C2970000425B
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