Global InformationCyclononatetraene information
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| IUPAC name
Cyclonona-1,3,5,7-tetraene
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CAS Number
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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InChI
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SMILES
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| Properties | |
Chemical formula
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C9H10 |
| Molar mass | 118.179 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Cyclononatetraene is an organic compound with the formula C9H10. It was first prepared in 1969 by protonation of the corresponding aromatic anion (described below).[1] It is unstable and isomerizes with a half-life of 50 minutes at room temperature to 3a,7a-dihydro-1H-indene via a thermal 6π disrotatory electrocyclic ring closing.[2] Upon exposure to ultraviolet light, it undergoes a photochemical 8π electrocyclic ring closing to give bicyclo[6.1.0]nona-2,4,6-triene.[3]
- ^ Radlick, Phillip; Alford, Gary (November 1969). "Preparation and isolation of cis, cis, cis, cis-1,3,5,7-cyclononatetraene". Journal of the American Chemical Society. 91 (23): 6529–6530. doi:10.1021/ja01051a083. ISSN 0002-7863.[permanent dead link]
- ^ Radlick, Phillip; Gary Alford (1969), "Preparation and isolation of cis, cis, cis, cis-1,3,5,7-cyclononatetraene", Journal of the American Chemical Society, 91 (23): 6529–6530, doi:10.1021/ja01051a083
- ^ de Meijere, Armin, ed. (2014). Houben-Weyl Methods of Organic Chemistry Vol. E 17b, 4th Edition Supplement: Carbocyclic Three-Membered Ring Compounds, Cyclopropanes: Synthesis. Goettingen: Georg Thieme Verlag. p. 1226. ISBN 978-3131819543.