Cycloheptyne

Last updated
Cycloheptyne
Cycloheptyne.svg
Names
Preferred IUPAC name
Cycloheptyne
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C7H10/c1-2-4-6-7-5-3-1/h1-5H2
    Key: WAXSUAIGRGARIT-UHFFFAOYSA-N
  • C1CCC#CCC1
Properties
C7H10
Molar mass 94.157 g·mol−1
Density 0.9 g/cm³
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  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.