Cyclooctadecanonaene
| Cyclooctadecanonaene | |
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Annulene.svg) |
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Annulene-3D-balls.png) |
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| Identifiers | |
| CAS number | 2040-73-5  |
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| Properties | |
| Molecular formula | C18H18 |
| Molar mass | 234.34 g mol−1 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Cyclooctadecanonaene or [18]annulene is an annulene with chemical formula C18H18. This hydrocarbon obeys Hückel's rule and is, therefore, an aromatic compound. The compound was first synthesised by Franz Sondheimer.[1]
[edit] 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.[2] [3]
[edit] See also
[edit] References
- ^ In the literature and some internet references, Sondheimer is sometimes misspelled as Sandheimer.
- ^ Sondheimer, F., Wolovsky, R. and Amiel, Y. (1962). "Unsaturated Macrocyclic Compounds. XXIII. The Synthesis of the Fully Conjugated Macrocyclic Polyenes Cyclooctadecanonaene ([18]Annulene), Cyclotetracosadodecaene ([24]Annulene), and Cyclotriacontapentadecaene ([30]Annulene).". J. Am. Chem. Soc. 68 (2): 274–284. doi:10.1021/ja00861a030.
- ^ K. Stöckel and F. Sondheimer (1988), "[18]Annulene", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0068; Coll. Vol. 6: 68
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