Vinyl norbornene

Vinyl norbornene
Names
IUPAC name
5-Ethenylbicyclo[2.2.1]hept-1-ene
Other names
  • VNB
  • 5-vinyl-2-norbornene
  • 5-vinylbicyclo[2.2.1]hept-2-ene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Vinyl norbornene is an organic compound. It is used to make ethylidene norbornene, an ingredient in some types of rubber.

Preparation

Vinyl norbornene can be made from the Diels-Alder reaction of butadiene and cyclopentadiene.

Uses

The main use of vinyl norbornene is changing it into its isomer, ethylidene norbornene.

Vinyl norbornene can also be polymerised, making a homopolymer called polyvinyl norbornen.[1] Like other norbornenes, this is a regioselective reaction where the double bond inside the norbornene ring polymerises and the double bond on the vinyl group outside the ring does not.[2] The homopolymer is not commonly used, but vinyl norbornene can be used instead of ethylidene norbornene to make EPDA rubber copolymers.

  1. ↑ Wozniak, Alyona I.; Bermesheva, Evgeniya V.; Andreyanov, Fedor A.; Borisov, Ilya L.; Zarezin, Danil P.; Bakhtin, Danila S.; Gavrilova, Natalia N.; Ilyasov, Igor R.; Nechaev, Mikhail S.; Asachenko, Andrey F.; Topchiy, Maxim A.; Volkov, Alexey V.; Finkelshtein, Eugene Sh.; Ren, Xiang-Kui; Bermeshev, Maxim V. (2020). "Modifications of addition poly(5-vinyl-2-norbornene) and gas-transport properties of the obtained polymers". Reactive and Functional Polymers. 149 104513. Bibcode:2020RFPol.14904513W. doi:10.1016/j.reactfunctpolym.2020.104513.
  2. ↑ Wozniak, Alyona I.; Bermesheva, Evgeniya V.; Andreyanov, Fedor A.; Borisov, Ilya L.; Zarezin, Danil P.; Bakhtin, Danila S.; Gavrilova, Natalia N.; Ilyasov, Igor R.; Nechaev, Mikhail S.; Asachenko, Andrey F.; Topchiy, Maxim A.; Volkov, Alexey V.; Finkelshtein, Eugene Sh.; Ren, Xiang-Kui; Bermeshev, Maxim V. (2020). "Modifications of addition poly(5-vinyl-2-norbornene) and gas-transport properties of the obtained polymers". Reactive and Functional Polymers. 149 104513. Bibcode:2020RFPol.14904513W. doi:10.1016/j.reactfunctpolym.2020.104513.
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