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Revision as of 15:22, 18 April 2011

Cyclooctadecanonaene
Skeletal formula
Ball-and-stick model
Identifiers
CAS Number
InChI
  • InChI=1S/C18H18/c1-2-4-6-8-10-12-14-16-18-17-15-13-11-9-7-5-3-1/h1-18H/b2-1-,3-1+,4-2+,5-3+,6-4+,7-5-,8-6-,9-7+,10-8+,11-9+,12-10+,13-11-,14-12-,15-13+,16-14+,17-15+,18-16+,18-17-Key: STQWAGYDANTDNA-DWSNDWDZSA-N
Properties
Chemical formula C18H18
Molar mass 234.342 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Cyclooctadecanonaene or 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. 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.

References

  1. In the literature and some internet references Sondheimer is 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 (Annulene), Cyclotetracosadodecaene (Annulene), and Cyclotriacontapentadecaene (Annulene)". J. Am. Chem. Soc. 68 (2): 274–284. doi:10.1021/ja00861a030.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. K. Stöckel and F. Sondheimer (1988). "Annulene". Organic Syntheses; Collected Volumes, vol. 6, p. 68.
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