1,2,3-Cyclohexatriene

1,2,3-Cyclohexatriene
Names
	IUPAC name Cyclohexa-1,2,3-triene
Identifiers
CAS Number	90866-90-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:195206;
PubChem CID	22138104;
CompTox Dashboard (EPA)	DTXSID70622773 ;
	InChI InChI=1S/C6H6/c1-2-4-6-5-3-1/h1,6H,2,4H2 Key: LQABCMYNMHGWFU-UHFFFAOYSA-N;
	SMILES C1CC=C=C=C1;
Properties
Chemical formula	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). Infobox references

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.

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

^ "Benzene's forgotten isomer takes centre stage in organic synthesis". May 2, 2023.
^ 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.
^ 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.
^ "A fresh look at 1,2,3-cyclohexatriene shows it could be used as a versatile reagent in organic synthesis". May 3, 2023.

[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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