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 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.
Allikas: Https://en.wikipedia.org/wiki/1,2,3-Cyclohexatriene
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