✦ LIBER ✦
Planarization of 8π Rings. I. Confirmation of a speculation by Ermer on the ground state of a strained cyclooctatetraene and studies on analogous oxepins
✍ Scribed by Carl Trindle
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 275 KB
- Volume
- 67
- Category
- Article
- ISSN
- 0020-7608
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✦ Synopsis
We describe by ab initio calculations several rings containing eight electrons, forced into planarity by altering the balance of strain with fused rings. These include a tricyclic fused-cyclopropano ring derivative of cyclooctatetraene suggested by Ermer to be planar in its ground state, an analogous tricyclic oxepin, and cyclobutano ring-fused cyclooctatetraene previously described experimentally. We verify that cyclopropano ring fusion planarizes rings with eight electrons; however, by bond alternation and magnetic susceptibility suppression, forming the planar ring leaves the system anti-aromatic.