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Names | |
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Preferred IUPAC name Cyclononyne | |
Identifiers | |
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Properties | |
C9H14 | |
Molar mass | 122.211 g·mol−1 |
Density | 0.8972 g/cm³ |
Boiling point | 68 |
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]
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]
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]