1,2,3-Cyclohexatriene

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1,2,3-Cyclohexatriene
1,2,3-cyclohexatriene v2.svg
Names
IUPAC name
Cyclohexa-1,2,3-triene
Identifiers
3D model (JSmol)
ChEBI
PubChem CID
  • InChI=1S/C6H6/c1-2-4-6-5-3-1/h1,6H,2,4H2
    Key: LQABCMYNMHGWFU-UHFFFAOYSA-N
  • C1CC=C=C=C1
Properties
C6H6
Molar mass 78.114 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,2,3-Cyclohexatriene is an unstable chemical compound with the molecular formula C6H6. [1] It is an unusual isomer of benzene in which the three double bonds are cumulated.

This highly strained compound was first prepared in 1990, by reacting a cyclohexadiene derivative with cesium fluoride. [2] The product was too reactive to be isolated on its own, so its existence was confirmed by trapping via a cycloaddition reaction.

Preparation and trapping of 1,2,3-cyclohexatriene 1,2,3-cyclohexatriene reaction.svg
Preparation and trapping of 1,2,3-cyclohexatriene

1,2,3-Cyclohexatriene and its derivatives undergo a variety of reactions including cycloadditions, nucleophilic additions, and σ-bond insertions, [3] and therefore they can be versatile reagents for organic synthesis. [4]

References

  1. ↑ "Benzene's forgotten isomer takes centre stage in organic synthesis". May 2, 2023.
  2. ↑ Shakespeare, William C.; Johnson, Richard P. (1990). "1,2,3-cyclohexatriene and cyclohexen-3-yne: Two new highly strained C6H6 isomers". Journal of the American Chemical Society. 112 (23): 8578–8579. Bibcode:1990JAChS.112.8578S. doi:10.1021/ja00179a050.
  3. ↑ Kelleghan, Andrew V.; Bulger, Ana S.; Witkowski, Dominick C.; Garg, Neil K. (2023). "Strain-promoted reactions of 1,2,3-cyclohexatriene and its derivatives". Nature. 618 (7966): 748–754. Bibcode:2023Natur.618..748K. doi:10.1038/s41586-023-06075-8. PMC   10460091 . PMID   37075803. S2CID   258237506.
  4. ↑ "A fresh look at 1,2,3-cyclohexatriene shows it could be used as a versatile reagent in organic synthesis". May 3, 2023.
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