engleski

Pyramidalized Olefins: A DFT Study of bicyclo-[2.1.1], -[3.2.1] and -[3.2.2] Alkenes and their Fused Derivatives

Density functional theory (B3LYP/6-31G*) was used to study a large series of bridged polycyclic alkenes based on the bicyclo-[2.1.1], -[3.2.1], and -[3.2.2] nuclei. In those compounds with pi-facial dissymmetry, butterfly bending of the strained olefinic bonds were generally predicted. Surprisingly, large pyramidalizations are calculated for the highly strained but pi-facially symmetric tetracyclo[5.1.1.13, 5.02, 6]dec-2-ene (19.8°) and tetracyclo[5.2.2.13, 5.02, 6]dodec-2, 8, 10-triene(14.4°). The preference for propano-directed bending in the bicyclo[3.2.1]octenes is about as strong as that for endo bending in norbornenes.

DFT calculations; pyramidalization

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