Misplaced Pages

Cyclooctadecanonaene: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editNext edit →Content deleted Content addedVisualWikitext
Revision as of 10:25, 23 April 2010 editRifleman 82 (talk | contribs)Extended confirmed users32,435 edits name in lede← Previous edit Revision as of 12:51, 23 May 2010 edit undoDavshul (talk | contribs)Autopatrolled, Pending changes reviewers18,691 edits created WikilinkNext edit →
Line 28: Line 28:
| Autoignition = }} | Autoignition = }}
}} }}
'''Cyclooctadecanonaene''' or '''annulene''' is an ] with chemical formula C<sub>18</sub>H<sub>18</sub>. This ] obeys ] and is therefore an ] compound. The compound was first synthesised by F. Sondheimer.<ref>In the literature and some internet references Sondheimer is misspelled as Sandheimer.</ref> The original synthesis started by the ] of the di-] 1,5-hexadiyne with ] in ] to give the trimer, followed by ] and ] with ] ] in ] and was concluded with ] ] with the ].<ref>{{OrgSynth | title = <nowiki>Annulene</nowiki> | author = K. Stöckel and F. Sondheimer | collvol = 6 | collvolpages = 68 | year = 1988 | prep = cv6p0068}}</ref> '''Cyclooctadecanonaene''' or '''annulene''' is an ] with chemical formula C<sub>18</sub>H<sub>18</sub>. This ] obeys ] and is therefore an ] compound. The compound was first synthesised by ].<ref>In the literature and some internet references Sondheimer is misspelled as Sandheimer.</ref> The original synthesis started by the ] of the di-] 1,5-hexadiyne with ] in ] to give the trimer, followed by ] and ] with ] ] in ] and was concluded with ] ] with the ].<ref>{{OrgSynth | title = <nowiki>Annulene</nowiki> | author = K. Stöckel and F. Sondheimer | collvol = 6 | collvolpages = 68 | year = 1988 | prep = cv6p0068}}</ref>


==References== ==References==

Revision as of 12:51, 23 May 2010

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). 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. K. Stöckel and F. Sondheimer (1988). "Annulene". Organic Syntheses; Collected Volumes, vol. 6, p. 68.
Category: