Abstract
A MNDO and AM1 study of the isomerization of pyrans, thiopyrans, dihydropyridines, and their methoxy derivatives was carried out so as to clarify the nature of the effects causing the observed thermodynamic regioselectivity in nucleophilic addition to pyridinium, pyrylium and thiopyrylium cations. The results show that, in contrast to 2H-thiopyrans, 2H-pyrans and 1,2-dihydropyridines are significantly stabilized by a generalized anomeric effect when the group bonded to the 2 position is OMe
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