Strain-promoted reactions of 1,2,3-cyclohexatriene and its derivatives

Andrew V. Kelleghan, Ana S. Bulger, Dominick C. Witkowski and Neil K. Garg ()
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Andrew V. Kelleghan: University of California, Los Angeles
Ana S. Bulger: University of California, Los Angeles
Dominick C. Witkowski: University of California, Los Angeles
Neil K. Garg: University of California, Los Angeles

Nature, 2023, vol. 618, issue 7966, 748-754

Abstract: Abstract Since 18251, compounds with the molecular formula C6H6—most notably benzene—have been the subject of rigorous scientific investigation2–7. Of these compounds, 1,2,3-cyclohexatriene has been largely overlooked. This strained isomer is substantially (approximately 100 kcal mol−1) higher in energy compared with benzene and, similar to its relatives benzyne and 1,2-cyclohexadiene, should undergo strain-promoted reactions. However, few experimental studies of 1,2,3-cyclohexatriene are known8–12. Here 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, the integration of 1,2,3-cyclohexatrienes into multistep syntheses demonstrates their use in rapidly assembling topologically and stereochemically complex molecules. Collectively, these efforts should enable further investigation of the strained C6H6 isomer 1,2,3-cyclohexatriene and its derivatives, as well as their application in the synthesis of important compounds.

Date: 2023
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DOI: 10.1038/s41586-023-06075-8

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