1,2,3-Cyclohexatriene

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
1,2,3-Cyclohexatriene
Names
Preferred IUPAC name
Cyclohexa-1,2,3-triene
Identifiers
3D model (JSmol)
ChEBI
  • 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 Â°C [77 Â°F], 100 kPa).
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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

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