Bissecododecahedraenes, Unusual Hyperstable Olefins

Abstract

In the bissecododecahedradienes 3 and 4 generated from the tailor-made pagodanes 1 and 2, respectively, an ideal colinear orientation of the π orbitals and very small transannular separation leads to an unusually strong π-π interaction, which can be detected PE- and UV-spectroscopically. Only one of the two CC bonds in 3/4 can be catalytically hydrogenated. The “hyperstable” monoenes 5/6, however, can be epoxidized and cyclopropanated.