The preparation of a specifically deuterated cyclohexane and some methyl‐cyclohexanes by selective cis‐addition of hydrogen to perdeuterated cyclohexene and 1‐, 3‐, and 4‐methylcyclohexene is reported. The deuterium decoupled proton magnetic resonance spectra of these compounds are analyzed. The magnitude of the deuterium isotope effect is determined. The coupling constants show that no ring distortion is caused by the equatorial methyl group. There is an anomalous shift to higher field of the axial ring protons vicinal to the equatorial methyl group. This explains the absorptions at exceptionally high field observed for some di‐ and tri‐methylcyclohexanes.
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Remijnse et al. (1970) studied this question.
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