Cyclooctadecanonaene

Cyclooctadecanonaene
Identifiers
CAS number 2040-73-5
Properties
Molecular formula C18H18
Molar mass 234.34 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

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]

See also

References

  1. ^ In the literature and some internet references, Sondheimer is sometimes misspelled as Sandheimer.
  2. ^ 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. 
  3. ^ K. Stöckel and F. Sondheimer (1988), "[18]Annulene", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0068 ; Coll. Vol. 6: 68