Abstract
Semiempirical methods have been used to locate the stationary points on the potential energy surface for the reaction of endoand exotricyclo[3.2.1.0 2.4]octanes ( 1) and ( 2) with protonated methanol. The calculations show a thermodynamic preference for rupture of the C2C4 bond. The corner transition states for cleavage of the C2C4 bonds show elongation of both the C2C4 and C2C3 cyclopropyl bonds. This is consistent with interaction of the incoming protonated methanol with both the HOMO and HOMO-1 Orbitals of the cyciopropanes. For edge attack the semiempirical transition states show elongation of the C2C4 bonds, but not of the C2C3 bonds. Mapping of the HOMO and HOMO-1 orbitals on to the electron density surface provides a simple method of predicting reaction stereochemistry.
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