Cyclononyne

Last updated
Cyclononyne
Cyclononyne.png
Names
Preferred IUPAC name
Cyclononyne
Identifiers
3D model (JSmol)
1920441
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C9H14/c1-2-4-6-8-9-7-5-3-1/h1-7H2
    Key: WXUICIMSUQBFMI-UHFFFAOYSA-N
  • C1CCCC#CCCC1
Properties
C9H14
Molar mass 122.211 g·mol−1
Density 0.8972 g/cm³
Boiling point 68 °C (154 °F; 341 K) at 15 Torr
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyclononyne is an organic compound with the chemical formula C9H14. [1] Its molecule has a ring of nine carbon atoms, connected by eight single bonds and one triple bond. [2]

Contents

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 C9 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

  1. ↑ 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. Retrieved 8 August 2025.
  2. ↑ 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. Bibcode:1979JMoSt..56...77T. doi:10.1016/0022-2860(79)80139-8. ISSN   0022-2860 . Retrieved 8 August 2025.
  3. ↑ Dodziuk, Helena (30 March 2009). Strained Hydrocarbons: Beyond the van't Hoff and Le Bel Hypothesis. John Wiley & Sons. p. 386. ISBN   978-3-527-62714-1 . Retrieved 8 August 2025.
  4. ↑ 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 . Retrieved 8 August 2025.
  5. ↑ 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" . Synthesis . 48 (18): 3107–3119. doi:10.1055/s-0035-1561452. ISSN   0039-7881 . Retrieved 8 August 2025.
  6. ↑ Gajewski, Joseph J. (19 March 2004). Hydrocarbon Thermal Isomerizations. Elsevier. p. 316. ISBN   978-0-08-047298-0 . Retrieved 8 August 2025.
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