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cyclooctatetraene
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cyclooctatetraene

chemical compound
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Quick Summary

Cyclooctatetraene (C8H8) is a liquid unsaturated cyclic hydrocarbon. While it shares a cyclic, conjugated structure with benzene, it is significantly more reactive. It was first synthesized in 1911 and later a more direct synthesis from acetylene was developed.12

Unlike benzene, cyclooctatetraene does not possess the special stability required to be classified as aromatic. Structural studies reveal alternating single and double bonds and a nonplanar, tub-shaped structure. This prevents the delocalization of its eight π electrons, leading to reactivity more akin to an alkene than an aromatic compound.2

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2 Britannica Sources
  1. cyclooctatetraene
  2. hydrocarbon - Annulenes and the Hückel rule

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