Abstract
The synthesis of silicon-containing monomers, norbornenes, norbornadienes and tricyclo nonenes, is an important step in the design of highly permeable polymeric materials. The monomer structure determines its activity in the polymerization process. The key method in the synthesis of silicon-substituted norbornene (NB) and norbornadiene (NBD) monomers is [4π + 2π]-cycloaddition of Si-substituted ethylenes and acetylenes to cyclopentadiene (CPD) (or dicyclopentadiene, DCPD). This reaction, Diels–Alder diene condensation, is a classic and effective route to norbornene and its derivatives. Norbornenylchlorosilanes obtained via diene condensation are typically involved in further substitution of a chlorine atom by alkyl, alkoxy or other substituents. Exo-tricyclo non-7-enes (exo-tricyclononenes, TCNs) can be considered as norbornene derivatives containing a fused cyclobutane ring. Quadricyclane (Q) is a strained saturated hydrocarbon isomeric to norbornadiene-2,5 (NBD). Several alkenes with two Si-containing groups have been successfully involved in the cycloaddition reaction with Q.
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