Keep Going with Cyclooctatetraene!

• Addison Ault ^[1]
  1. [1] Cornell College

     Cornell College

     Township of Franklin, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 77, Nº 1 (January), 2000, págs. 55-55
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • This paper shows how some simple properties of cyclooctatetraene can indicate important ideas about the structure of cyclooctatetraene. Its heat of hydrogenation indicates no significant stabilization by delocalization of electrons, and its alternating carbon-carbon bond lengths are consistent with the presence of alternating "ordinary" single and double bonds. The nonplanar nature of cyclooctatetraene is conclusively indicated by the diastereotopic nature of the methyl groups in its dimethylcarbinyl derivative, illustrating one way that NMR can reveal subtle details of molecular structure. Finally, the Diels-Alder reaction provides a simple but elegant illustration of how reaction mechanisms can be deduced.