Cyclooctadecanonaene
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| Ball-and-stick model of the cyclooctadecanonaene molecule | |
| Identifiers | |
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| ChemSpider | 120988  |
| Jmol 3D model | Interactive image |
| PubChem | 137294 |
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| Properties | |
| C18H18 | |
| Molar mass | 234.34 g·mol−1 |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Cyclooctadecanonaene or [18]annulene is an annulene with chemical formula C
18H
18. This hydrocarbon obeys Hückel's rule and is, therefore, an aromatic compound. Theoretical studies show that [18]annulene has only three completely delocalized π bonds associated with its aromaticity, while other six π bonds represent the conjugated 3c-2e π bonds on the periphery of [18]annulene.[1] The compound was first synthesised by Franz Sondheimer.[2]
Reactions
The original synthesis started by the Eglinton reaction of the di-alkyne 1,5-hexadiyne with copper(II) acetate in pyridine to give the trimer, followed by deprotonation and isomerization with potassium tert-butoxide in tert-butanol and was concluded with hydrogen organic reduction with the Lindlar catalyst.[3] [4]
See also
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ In the literature and some internet references, Sondheimer is sometimes misspelled as Sandheimer.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
