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Synthesis and properties of bicyclo[ 5.2.0]nonatetraenyl anions. A new 10 π-electron system

✍ Scribed by Masaji Oda; Takashi Watabe; Takeshi Kawase

Book ID
104234449
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
241 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

Phenyl-and 8,9-diphenylbicyclo[5.2.O]nonatetraenyl anion, obtained in fairly stable solutions by base treatment of the corre-Toyonaka, Osaka 560, Japan sponding bicyclo[5.2.0]nona-1,3,5,8-tetraenes, display properties characteristic of aromatic systems. Recently we have reported the synthesis and X-ray crystal structure of bicyclo[6.2.0ldecapentaenes (1j.l The results suggest, in contrast with the transient nature of butalene3 and the nonplanar, polyolefinic nature of octalene, 4 that the aromatic stabilization of 1 asa peripheral 4ni2 n-electron system prevails over the antiaromatic destabilization of the component 4n n-electron rings, counterbalancing enough the strain energy associated with

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9-phenylbicyclo[6.1.0]nonatetraenyl anio
9-phenylbicyclo[6.1.0]nonatetraenyl anion: A new diatropic 10 π-electron system
✍ Takeshi Kawase; Masaji Oda 📂 Article 📅 1982 🏛 Elsevier Science 🌐 French ⚖ 146 KB

Swmary : Treatment of 9-chloro-9-phenylbicyclo[6.l.O]nona-2,4,6-triene with excess bases gives, by the intermediacy f 9-phenylbicyclor6.1.01-1(9),2,4,6\_tetraene, 9-phenylbicycloC6.1.O]tetraenyl anion of which 9 H-NMR spectrum suggests some diatropic character of the molecule.