Molecular mechanical analysis of the structure of strained organic molecules Communication 5. Trans-bicyclo[n.1.0.]alkanes and their derivatives
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According to the molecular mechanical method, MM/2, the trans isomers of bicyclo [4.1.0]heptane and bicyclo[3.1.0]hexane are destabilized by 10–30 kcal/mole relative to the respective cis bicycles, whereas bicyclo[2.1.0]pentane lacks the minimum corresponding to the trans isomer.
Both the MM/2 method and quantum chemical calculations disclose the possibility of existence of the trans isomer of bicyclo[1.1.0]butane with an HC1C3H dihedral angle of 180°, and of a still more strained structure with an inverted configuration of the two bridge C atoms.
The relation between trans-bicyclo[1.1.0]butane derivatives and a pyramid structure has been analyzed, and possible routes to the fixing of the trans-bicyclo[1.1.0]butane skeleton in a polycyclic structural framework have been proposed.
KeywordsAlkane Pyramid Pentane Butane Quantum Chemical
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