Abstract
The conformation of several trans -2,3-diaryloxy-1,4-dioxanes has been studied using 1H NMR techniques. Trans -2,3-bis(4-nitrophenoxy)-1,4-dioxane and trans -2,3-bis(4-methoxyphenoxy)-1,4-dioxane have been found to be predominantly ( ≈98%) in diaxial conformation in CDCl 3). On the other hand, trans -2,3-bis(2,6-dimethylphenoxy)-1,4-dioxane exists in the same conditions as a 66:33 mixture of diaxial and diequatorial conformers. An explanation based on the fulfilment of the exo-anomeric effect is provided.
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