Cycloheptyne

Cycloheptyne
Names
	Preferred IUPAC name Cycloheptyne
Identifiers
CAS Number	6577-09-9;
3D model (JSmol)	Interactive image;
ChemSpider	9063096;
PubChem CID	10887832;
	InChI InChI=1S/C7H10/c1-2-4-6-7-5-3-1/h1-5H2 Key: WAXSUAIGRGARIT-UHFFFAOYSA-N;
	SMILES C1CCC#CCC1;
Properties
Chemical formula	C7H10
Molar mass	94.157 g·mol−1
Density	0.9 g/cm³
Related compounds
Related compounds	Cyclobutyne; Cyclopentyne; Cyclooctyne; Cycloheptene; Cycloheptane;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cycloheptyne is an organic compound from the group of cycloalkynes with the chemical formula C₇H₁₀.^[1] It is a cyclic molecule containing a carbon-carbon triple bond within a seven-membered ring. This ring structure makes the molecule strained.^[2]^[3]

Synthesis

Cycloheptyne can be prepared starting from N, N'-diisopropylcycloheptane-1,2-diimine. By reaction with ammonia and hydroxylamine-O-sulfonic acid in methanol and subsequent reaction with silver(I) oxide; this is converted into a spiro compound with two diazirine rings. Heating or irradiation of this compound leads to the elimination of two molecules of nitrogen to form cycloheptyne.

An alternative synthesis method starts from cycloheptanone. This is first reacted with lithium diisopropylamide and para-tolyl-para-toluenethiosulfonate to introduce a sulfide unit. An enol triflate is then formed using potassium hexamethyldisilazide and bis(trifluoromethanesulfonyl)aniline, and the sulfide group is oxidized to the sulfoxide with meta-chloroperbenzoic acid.

References

^ Dodziuk, Helena (30 March 2009). Strained Hydrocarbons: Beyond the van't Hoff and Le Bel Hypothesis. John Wiley & Sons. p. 384. ISBN 978-3-527-62714-1. Retrieved 7 August 2025.
^ Schulte, Petra; Schmidt, Gunther; Kramer, Claus-Peter; Krebs, Adolf; Behrens, Ulrich (1 March 1997). "Metallorganische Verbindungen des Kupfers XIII. Kupfer(I)-chlorid-Komplexe winkelgespannter Cycloheptine Synthesen und Röntgenstrukturanalysen". Journal of Organometallic Chemistry. 530 (1): 95–100. doi:10.1016/S0022-328X(96)06605-3. ISSN 0022-328X. Retrieved 7 August 2025.
^ Hoffmann, Reinhard W. (2 December 2012). Dehydrobenzene and Cycloalkynes. Elsevier. p. 346. ISBN 978-0-323-16280-7. Retrieved 7 August 2025.

[1] Dodziuk, Helena (30 March 2009). Strained Hydrocarbons: Beyond the van't Hoff and Le Bel Hypothesis. John Wiley & Sons. p. 384. ISBN 978-3-527-62714-1. Retrieved 7 August 2025.

[2] Schulte, Petra; Schmidt, Gunther; Kramer, Claus-Peter; Krebs, Adolf; Behrens, Ulrich (1 March 1997). "Metallorganische Verbindungen des Kupfers XIII. Kupfer(I)-chlorid-Komplexe winkelgespannter Cycloheptine Synthesen und Röntgenstrukturanalysen". Journal of Organometallic Chemistry. 530 (1): 95–100. doi:10.1016/S0022-328X(96)06605-3. ISSN 0022-328X. Retrieved 7 August 2025.

[3] Hoffmann, Reinhard W. (2 December 2012). Dehydrobenzene and Cycloalkynes. Elsevier. p. 346. ISBN 978-0-323-16280-7. Retrieved 7 August 2025.

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