 | |
| Names | |
|---|---|
| Preferred IUPAC name Cyclodecyne | |
| Other names 1-Cyclodecyne | |
| Identifiers | |
3D model (JSmol) | |
| 2203338 | |
| ChEBI | |
| ChemSpider | |
| |
| |
| 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 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Cyclodecyne is an organic compound with the chemical formulaC10H16.[1][2] The molecule has a ring of 10 carbon atoms, connected by nine single bonds and onetriple bond.[3]
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 doubledehydrohalogenation of1,2-dibromocyclodecane using a strong base such aspotassium hydroxide (KOH) orsodium amide (NaNH2) in a high-boiling solvent:[4]
Alternatively,Fritsch–Buttenberg–Wiechell rearrangement of suitabledibromovinyl precursors has been used to generate cyclodecyne under milder conditions.[5]
Due to its reactivity, cyclodecyne is often generatedin situ and trapped incycloaddition reactions rather than stored for long periods.
