Chemistry:Cyclononyne
Cyclononyne is an organic compound with the chemical formula C
9H
14.[1] Its molecule has a ring of nine carbon atoms, connected by eight single bonds and one triple bond.[2]
Synthesis
The compound can be prepared by converting 1,2-cyclononanedione to the corresponding dihydrazone via hydrazine and then reacting it with mercuric oxide in the presence of sodium sulfate.[3][4] When 1,2-cyclononadiene is exposed to light in a dilute pentane solution, it will produce a small amount of cyclononyne and other C
9 cycloolefin products via the intermediate isomer of bicyclo[6.1.0]non-8-ene. Under the catalysis of a rhodium complex, it is refluxed with sulfur in butanone to obtain a dithiol derivative, which is then refluxed in o-dichlorobenzene and desulfurized to obtain a thiophene derivative.[5]
Physical properties
It is reported that pyrolysis of cyclononyne at 600 °C will lead to forming 1,2,8-nonatriene and trans-bicyclo[4.3.0]nona-2-ene in a 1:0.9 ratio.[6]
References
- ↑ Turner, R. B.; Jarrett, A. D.; Goebel, P.; Mallon, B. J. (1973). "Heats of hydrogenation. 9. Cyclic acetylenes and some miscellaneous olefins". NIST. pp. 790–792. https://webbook.nist.gov/cgi/cbook.cgi?ID=C6573520&Mask=8.
- ↑ Typke, V.; Haase, J.; Krebs, A. (1 January 1979). "The molecular structure of cyclononyne: a gas phase electron diffraction investigation". Journal of Molecular Structure 56 (1): 77–86. doi:10.1016/0022-2860(79)80139-8. ISSN 0022-2860. Bibcode: 1979JMoSt..56...77T. https://www.sciencedirect.com/science/article/abs/pii/0022286079801398. Retrieved 8 August 2025.
- ↑ Dodziuk, Helena (30 March 2009) (in en). Strained Hydrocarbons: Beyond the van't Hoff and Le Bel Hypothesis. John Wiley & Sons. p. 386. ISBN 978-3-527-62714-1. https://books.google.com/books?id=rpPULNO9XN4C&dq=Cyclononyne&pg=PA386. Retrieved 8 August 2025.
- ↑ Prelog, V.; Schenker, K; Kung, W. (1953). "Carbon rings. LXII. The oxidation of cyclononene to 1,5-cyclononanediols, a transanular reaction". Helvetica Chimica Acta (36): 471–482. doi:10.1002/hlca.19530360216. ISSN 0018-019X. https://www.worldcat.org/search?fq=x0:jrnl&q=n2:0018-019X. Retrieved 8 August 2025.
- ↑ Arisawa, Mieko; Ichikawa, Takuya; Tanii, Saori; Yamaguchi, Masahiko (September 2016). "Synthesis of Symmetrical and Unsymmetrical 1,4-Dithiins by Rhodium-Catalyzed Sulfur Addition Reaction to Alkynes" (in en). Synthesis 48 (18): 3107–3119. doi:10.1055/s-0035-1561452. ISSN 0039-7881. https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0035-1561452. Retrieved 8 August 2025.
- ↑ Gajewski, Joseph J. (19 March 2004) (in en). Hydrocarbon Thermal Isomerizations. Elsevier. p. 316. ISBN 978-0-08-047298-0. https://books.google.com/books?id=fxopSfH0WTIC&dq=Cyclononyne&pg=PA316. Retrieved 8 August 2025.
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