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Updated: Sep 19, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Nonradical Reactions of p-Benzyne Diradicals
1Department of Chemistry, University of California─San Diego, La Jolla, California 92093-0358, United States.
Abstract:
Enediynes undergo electrocyclization to p-benzyne diradicals. Although such diradicals ordinarily react by radical pathways, they can also be trapped by nucleophilic addition, a pathway supported by computations. The product of that addition is a "naked" aryl anion that is unselective toward protonation. A cyclohexeno-substituted enediyne was synthesized and found to be more amenable to further derivatization and mechanistic study. Moreover, it was shown to undergo automerization, rearrangement to a degenerate form of the original enediyne.
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