1,2,3-Cyclohexatriene is an unstable chemical compound with the molecular formula . It is an unusual
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
of
benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
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. 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
cycloaddition
In organic chemistry, a cycloaddition is a chemical reaction in which "two or more Unsaturated hydrocarbon, unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of th ...
s,
nucleophilic addition
In organic chemistry, a nucleophilic addition (AN) reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic addit ...
s, and
σ-bond insertions, and therefore they can be versatile
reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
s for
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
.
References
{{DEFAULTSORT:Cyclohexatriene, 1,2,3-
Benzene
Isomerism