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.^[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 (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.

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. 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. 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.

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