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The stereochemical aspects of epoxidation of norbornene and its 7- syn -substituted derivatives by performic acid were investigated. Geometry and thermodynamic parameters of transition states and prereactive complexes were computed at the UBHandHLYP/6-31G(d) level of theory. It is shown that the transition states have a pronounced biradical character and a nearly coplanar orientation of the C=C bond and the molecule of performic acid. Transition state analysis revealed that, in the case of the syn -7-hydroxy derivative, the preference for the exo -approach of the oxidant can be explained by the stabilization of transition state with hydrogen bonding. In contrast, a chlorine atom or a methyl group at the 7- syn position facilitated the formation of endo -epoxides due to steric repulsion between the substituent and the oxidant.

Стереохімія епоксидування біцикло[2.2.1]гепт-2-єнів та їх 7-syn-заміщених похідних. Дослідження методом DFT