Study On The Synthesis Of 1,1'-bipentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]Undecane

Pentacyclo[5.4.0.02,6.03,10.05,9]undecane(formula C11H14,PCU) is a caged hydrocarbon compound with high density and high combustion value. PCU's density is 1.23 g/cm3, and its combustion value is 51.66 MJ/L. Because of its volatility, PCU is not suitable for using direc-tly as the rocket solid fuel, but as a a high-energy compound additive to increase the overall combustion performance of complex fuels while added into liquid fuels. From the foreign reports, under the circumstances of that PCU's original density and combustion value can be guaranteed, PCU dimer can solve PCU's volatility quite well. But the preparation required a large amount of titanium as a catalyst, which increased preparation costs. Also, the excessive reaction steps can result in low yield of the whole reaction. So designing and preparing new caged hydrocarbon compounds seem to have important research significance. So far, the reports of preparation of 1,1'-bipentacyclo[5.4.0.02,6.03,10.05,9]undecane, whose structure is similar to PCU dimer,are few from home and abroad. Exploring to prepare new caged hydrocarbon compounds like 1,1'-bipentacyclo[5.4.0.02,6.03,10.05,9]undecane may have great research values and meanings.Choosing the proper starting materials is the key to design the preparation of such kind of biPCU. This paper conducted a preliminary exploration on synthesis of 1,1,-bipentacyclo[5.4.0.02,6.03,10.05,9]undecane, and designed a synthesis route, choosing 2,2'-biphenol as the stating material, and aiming to prepare target product compound through Diels-Alder addition reaction, [2+2]cycloaddition reaction, and Wolff-Kishner-Huang reduction reaction these three reaction steps.This paper first optimized the Wolff-Kishner-Huang reduction conditions of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-dione(formula C11H1002, PCUD), lowing the reaction temperature, and improving the reaction yield. Based on that, this paper then investigates the three important reaction steps, optimized the synthesis route, confirmed the optimum condition:during the Diels-Alder addition reaction of compound 2 with cyclopentadiene, when the reaction temperature is-20 ?, and n(compound 2):n(cyclopentadiene)=1:4, the reaction yield is 85.5%;Optimum conditions of [2+2] cycloaddition on yield was also studied. While choosing pure Ethyl acetate as the solvent, and 1.5 h as the irradiation time, the yield of [2+2] cycloaddition can reach to 90.0%; after the Wolff-Kishner-Huang reduction from compound 4, target product compound 1 wasn't prepared unexpectedly. The possible reason that the preparation failed is the reduction might need higher reaction temperature to react. The conditions of reduction reaction require further exploration. Besides, compound 4 has 4 carbonyl groups, while introducing other new specific functional groups, and compound 4 might be prepared to new caged hydrocarbon derivatives, which can be used in other ways. Studying these new caged hydrocarbon derivatives will be new research areas.