Cyclodecyne

Cyclodecyne
Names
	Preferred IUPAC name Cyclodecyne
	Other names 1-Cyclodecyne
Identifiers
CAS Number	3022-41-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2203338
ChEBI	CHEBI:37817;
ChemSpider	121452;
PubChem CID	137799;
CompTox Dashboard (EPA)	DTXSID70184321;
	InChI InChI=1S/C10H16/c1-2-4-6-8-10-9-7-5-3-1/h1-8H2 Key: BGMJEAAFHCTKBY-UHFFFAOYSA-N;
	SMILES C1CCCCC#CCCC1;
Properties
Chemical formula	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	Cyclopentyne; Cyclooctyne; Cyclononene; Cyclononane;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cyclodecyne is an organic compound with the chemical formula C₁₀H₁₆. The molecule has a ring of 10 carbon atoms, connected by nine single bonds and one triple bond.

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:

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.

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. Bibcode:1951JAChS..73.5510B. doi:10.1021/ja01155a575. ISSN 0002-7863. Retrieved 9 August 2025.
↑ "Cyclodecyne". NIST. Retrieved 9 August 2025.
↑ "Cyclodecyne properties - SpringerMaterials". Springer Publishing. Retrieved 9 August 2025.
↑ Luisa, Bozzano G. (2 December 2012). Organic Functional Group Preparations: Volume 1. Academic Press. p. 92. ISBN 978-0-08-092556-1. 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". Nature Communications. 15 (1): 8313. Bibcode:2024NatCo..15.8313A. doi:10.1038/s41467-024-52390-7. ISSN 2041-1723. PMC 11436752. PMID 39333083.

[1] 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. Bibcode:1951JAChS..73.5510B. doi:10.1021/ja01155a575. ISSN 0002-7863. Retrieved 9 August 2025.

[2] "Cyclodecyne". NIST. Retrieved 9 August 2025.

[3] "Cyclodecyne properties - SpringerMaterials". Springer Publishing. Retrieved 9 August 2025.

[4] Luisa, Bozzano G. (2 December 2012). Organic Functional Group Preparations: Volume 1. Academic Press. p. 92. ISBN 978-0-08-092556-1. Retrieved 9 August 2025.

[5] 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". Nature Communications. 15 (1): 8313. Bibcode:2024NatCo..15.8313A. doi:10.1038/s41467-024-52390-7. ISSN 2041-1723. PMC 11436752. PMID 39333083.