Chemistry:Cyclodecyne
Cyclodecyne is an organic compound with the chemical formula C
10H
16.[1][2] The molecule has a ring of 10 carbon atoms, connected by nine single bonds and one triple bond.[3]
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 (NaNH
2) 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.
References
- ↑ Blomquist, A. T.; Burge, Robert E. Jr.; Liu, Liang Huang; Bohrer, James C.; Sucsy, Arthur C.; Kleis, John (1 November 1951). "Many-Membered Carbon Rings. Iv. Synthesis of Cyclononyne and Cyclodecyne". Journal of the American Chemical Society 73 (11): 5510–5511. doi:10.1021/ja01155a575. ISSN 0002-7863. Bibcode: 1951JAChS..73.5510B. https://pubs.acs.org/doi/10.1021/ja01155a575. Retrieved 9 August 2025.
- ↑ "Cyclodecyne" (in en). NIST. https://webbook.nist.gov/cgi/cbook.cgi?ID=C3022411&Mask=8.
- ↑ "Cyclodecyne properties - SpringerMaterials". Springer. https://materials.springer.com/substanceprofile/docs/smsid_pbeorzczgrpjpjxo.
- ↑ Luisa, Bozzano G. (2 December 2012) (in en). Organic Functional Group Preparations: Volume 1. Academic Press. p. 92. ISBN 978-0-08-092556-1. https://books.google.com/books?id=EiIdSriezKIC&dq=cyclodecyne+potassium+hydroxide&pg=PA92. Retrieved 9 August 2025.
- ↑ Anderson, T. E.; Thamattoor, Dasan M.; Phillips, David Lee (27 September 2024). "Probing the alkylidene carbene–strained alkyne equilibrium in polycyclic systems via the Fritsch–Buttenberg–Wiechell rearrangement" (in en). Nature Communications 15 (1): 8313. doi:10.1038/s41467-024-52390-7. ISSN 2041-1723. PMID 39333083. Bibcode: 2024NatCo..15.8313A.
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