Dimerization of highly pyramidalized 3,4,8,9-tetramethyltetracyclo[4.4.0.03,9.04,8]dec-1(6)-ene to a hydrocarbon featuring four cyclohexane rings in boat conformation

Abstract

The synthesis, chemical trapping, and dimerization of a highly pyramidalized alkene is reported. Its dimer is a unique nonacycle featuring three planar cyclobutane rings, four cyclopentane rings, and four cyclohexane rings in boat conformations. The X-ray diffraction analysis showed a H-H distance between the flagpole hydrogen atoms of 1.999 and a separation of 2.619 between the two flagpole carbon atoms. The three cyclobutane rings of the dimer were thermally stable