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Revision as of 10:34, 20 April 2011 edit14.139.160.2 (talk)No edit summary← Previous edit Revision as of 23:35, 20 April 2011 edit undoWhy Not A Duck (talk | contribs)Extended confirmed users, Rollbackers11,866 edits Undid revision 425000266 by 14.139.160.2 (talk) -- would its aromaticity actually depend on temperature? seems dubious. source or explanation?Next edit →
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'''Cyclooctadecanonaene''' or '''annulene''' is an ] with chemical formula C<sub>18</sub>H<sub>18</sub>. This ] obeys ] and is therefore an ] compound at room temperatures. 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>{{cite journal | title = Unsaturated Macrocyclic Compounds. XXIII. The Synthesis of the Fully Conjugated Macrocyclic Polyenes Cyclooctadecanonaene (Annulene), Cyclotetracosadodecaene (Annulene), and Cyclotriacontapentadecaene (Annulene). | author = Sondheimer, F., Wolovsky, R. and Amiel, Y. | journal = ] | year = 1962 | volume = 68 | issue = 2 | pages = 274–284 | doi = 10.1021/ja00861a030}}</ref> <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>{{cite journal | title = Unsaturated Macrocyclic Compounds. XXIII. The Synthesis of the Fully Conjugated Macrocyclic Polyenes Cyclooctadecanonaene (Annulene), Cyclotetracosadodecaene (Annulene), and Cyclotriacontapentadecaene (Annulene). | author = Sondheimer, F., Wolovsky, R. and Amiel, Y. | journal = ] | year = 1962 | volume = 68 | issue = 2 | pages = 274–284 | doi = 10.1021/ja00861a030}}</ref> <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 23:35, 20 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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