Abstract
Studies by both MM2 and ab initio MO methods indicate that the «anomeric effect» observed in carbohydrates and tetrahydropyrans (THP) is also present in 4-tetrahydropyranones (THPN). The α-methyl group in a 4-THPN ring favors the equatorial orientation to a greater extent (2.4 kcal/mol) than it would in a cyclohexane system. A 2-phenyl group has a modest preference (1.1 kcal/mol) for the equatorial orientation
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