Cyclodecyne
Chemical compound
From Wikipedia, the free encyclopedia
Cyclodecyne is an organic compound with the chemical formula C10H16.[1][2] The molecule has a ring of 10 carbon atoms, connected by nine single bonds and one triple bond.[3]
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| Names | |
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| Preferred IUPAC name
Cyclodecyne | |
| Other names
1-Cyclodecyne | |
| Identifiers | |
3D model (JSmol) |
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| 2203338 | |
| ChEBI | |
| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C10H16 | |
| Molar mass | 136.238 g·mol−1 |
| Density | 0.898 g/cm³ |
| Boiling point | 205 °C (401 °F; 478 K) |
| Related compounds | |
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
Cyclodecyne was first synthesized and isolated in the mid-20th century as part of studies on medium-ring hydrocarbons. A common synthetic route involves the double dehydrohalogenation of 1,2-dibromocyclodecane using a strong base such as potassium hydroxide (KOH) or sodium amide (NaNH2) in a high-boiling solvent:[4]
- 1,2-Dibromocyclodecane + 2KOH → cyclodecyne + 2KBr + 2H2O
Alternatively, Fritsch–Buttenberg–Wiechell rearrangement of suitable dibromovinyl precursors has been used to generate cyclodecyne under milder conditions.[5]
Physical properties
Due to its reactivity, cyclodecyne is often generated in situ and trapped in cycloaddition reactions rather than stored for long periods.