- Cyclooctadecanonaene
-
Cyclooctadecanonaene Identifiers CAS number 2040-73-5 - 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 Molecular formula C18H18 Molar mass 234.34 g mol−1 (verify) (what is: / ?)
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
- Superbenzene
References
- ^ In the literature and some internet references, Sondheimer is sometimes misspelled as Sandheimer.
- ^ 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.
- ^ K. Stöckel and F. Sondheimer (1988), "[18]Annulene", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0068; Coll. Vol. 6: 68
Categories:- Annulenes
- 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-
Wikimedia Foundation. 2010.