Nature research paper: Strain-promoted reactions of 1,2,3-cyclohexatriene and its derivatives
. Of these compounds, 1,2,3-cyclohexatriene has been largely overlooked. This strained isomer is substantially higher in energy compared to benzene and, like its relatives benzyne and 1,2-cyclohexadiene, should undergo strain-promoted reactions. However, few experimental studies of 1,2,3-cyclohexatriene are known. We demonstrate that 1,2,3-cyclohexatriene and its derivatives participate in a host of reaction modes including diverse cycloadditions, nucleophilic additions, and σ-bond insertions.
Experimental and computational studies of an unsymmetrical derivative of 1,2,3-cyclohexatriene demonstrate the potential for highly selective reactions of strained trienes despite their high reactivity and short lifetimes. Finally, integration of 1,2,3-cyclohexatrienes into multistep synthetic sequences demonstrates their utility in rapidly assembling topologically and stereochemically complex molecules.
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