Abstract
cis- and trans-2,5-Dimethoxytetrahydropyrans, cis-2,5-dimethoxy-6-methyltetrahydropyran and 2-methoxy-5-methyltetrahydropyran have been examined to see the effect of an OCH 3 group at position 5 on the degree of anomeric effect in substituted 2-methoxytetrahydropyrans. The present study shows that this group stabilises the C-2 electronegative substituent in the axial position. Semi-empirical and ab initio molecular orbital calculations support this view. AM1 calculation gives lower enthalpies as well as lower dipole moments for the compounds having an OCH 3 group in the axial position at C-2 over the equatorial form in 2-methoxytetrahydropyrans. This enhanced stabilisation is attributed to the electrostatic interaction between the partial positive charge at C-5 and the partial negative charge of the aglycone oxygen atom.
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