The changes induced in the chemical shifts of certain protons in some carbohydrate derivatives and some other poly-oxygenated compounds, on addition of sodium iodide to their solutions in acetone- d 6, are reported. The H-1 resonances of β-glycosides of 2,3- O-isopropylidene-4- O-methyl- L-rhamnopyranoside were significantly affected by the addition of sodium ions, whereas with the α- L-glycosides, these resonances were virtually unaltered. Methoxyacetaldehyde diethyl acetal, triethyl orthoformate, and tris(2-methoxyethyl) orthoformate all showed significant induced-shifts in their acetal-proton resonances on the addition of sodium ions, and all the proton resonances of 1,4-anhydroerythritol were affected, but to differing degrees. With the cis- and trans-5-methoxy-2-phenyl-1,3-dioxanes, it is the former isomer, which can in principle simultaneously use all three oxygen atoms in the molecule to complex a sodium ion, which shows the greatest induced-shift in the acetal-proton resonance.
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