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Cycloheptene

Cycloheptene is a 7-membered cycloalkene with a flash point of −6.7 °C. It is a raw material in organic chemistry and a monomer in polymer synthesis. Cycloheptene can exist as either the cis- or the trans-isomer. :[[File:Cycloheptene isomers.png|400px]]

''trans''-Cycloheptene

Under normal conditions, the cycloheptene double bond forms the cis isomer. However, the unstable trans isomer is an accessible reactive intermediate. Methyl benzoate catalyzes singlet photosensitization; irradiating cis-cycloheptene and it with ultraviolet light at −35 °C produces a detectible trans-cycloheptene population.

The anti-Bredt trans isomer is very strained, and the unsaturated carbons are partly pyramidal. The pyramidalization angle is estimated at 37° and the p orbital misalignment 30.1°. The isomer decomposes facily through a dimolecular, diradical pathway, even at temperatures too low for double-bond rotation.

References

References

  1. [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/141720 Cycloheptene] at [[Sigma-Aldrich]]
  2. (April 2004). "Conformational studies of ''trans''-cycloheptene, ''trans''-cycloheptene oxide, and ''trans''-bicyclo[5.1.0]octane by ab initio calculations". [[Journal of Molecular Structure: THEOCHEM]].
  3. (2005). "How Stable Is ''trans''-Cycloheptene?". [[J. Am. Chem. Soc.]].
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cycloalkenes monomers seven-membered-rings
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