Jump to content

Cyclooctadecanonaene

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Rifleman 82 (talk | contribs) at 10:25, 23 April 2010 (name in lede). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Cyclooctadecanonaene
Skeletal formula
Ball-and-stick model
Identifiers
  • 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
C18H18
Molar mass 234.342 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 F. Sondheimer.[1] 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]

References

  1. ^ In the literature and some internet references Sondheimer is misspelled as Sandheimer.
  2. ^ K. Stöckel and F. Sondheimer (1988). "[18]Annulene". Organic Syntheses; Collected Volumes, vol. 6, p. 68.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Cyclooctadecanonaene&oldid=357799334"