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Dicyclopenta[a,d]cyclooctene: A [14]Annulene Containing Two Zero-Atom Cross-Links
Mitsunori Oda1, Yukinari Sakamoto1, Takanori Kajioka1
1Department of Applied Chemistry, Faculty of Engineering Toyama University Gofuku 3190, Toyama 930-8555 (Japan) Fax: (+81) 76-445-6819.
Angewandte Chemie (International Ed. in English)
|May 2, 2018
Summary
Heating pentafulvene induces a 14π-electrocyclization, forming dicyclopenta[a,d]cyclooctene. This nonalternant hydrocarbon exhibits diatropic character and a unique absorption spectrum with a maximum at 767 nm.
Area of Science:
- Organic Chemistry
- Physical Chemistry
Background:
- Pentafulvene is a nonalternant hydrocarbon with reactive pentafulvenoid moieties.
- Electrocyclization reactions are key transformations in organic synthesis.
Purpose of the Study:
- To investigate the thermal electrocyclization of pentafulvene.
- To characterize the resulting dicyclopenta[a,d]cyclooctene product.
Main Methods:
- Heating pentafulvene to induce a 14π-electrocyclization reaction.
- Spectroscopic analysis (UV-Vis) to determine the electronic properties of the product.
Main Results:
- Successful synthesis of dicyclopenta[a,d]cyclooctene via thermal electrocyclization.
- The product exhibits diatropic character, indicating aromaticity.
- A distinctive absorption spectrum with a longest wavelength maximum at 767 nm was observed.
Conclusions:
- Thermal electrocyclization is an effective route to dicyclopenta[a,d]cyclooctene.
- The dicyclopenta[a,d]cyclooctene product possesses unique electronic and spectral properties.
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