Synthesis of 4,4′-bipentacyclo[5.4.0.02,6.03,10.05,9]undecane

Abstract

A new bi-cage hydrocarbon, 4,4′-bipentacyclo[5.4.0.02,6.03,10.05,9]undecane (12) was designed based on a strategy to construct two cages simultaneously from one key molecule scaffold. Thus 12 was conveniently synthesized from 5,5′-bi(cyclopentadiene) (9) through a three steps synthetic route in 23% overall yield. The new bi-cage hydrocarbon has high density (1.2322g/cm3) and high volumetric heat of combustion (51.670MJ/L).