Abstract
AbstractCycloaromatization reactions of enediynes are renowned for their widespread applications and interesting reactivity characteristics. In the presence of a lithium halide and a weak acid, the cycloaromatization of cyclodeca‐1,5‐diyn‐3‐ene can be redirected away from the usual formation of a phenyl diradical towards a zwitterionic pathway. We extended this zwitterionic reaction system to other enediyne compounds and found that it offered good applicability to all‐carbon systems. However, in the case of maleimide‐based enediynes, only diradical (phenyl‐substituted) or anionic (butyl‐substituted) cyclization pathways were observed. Notably, the nucleophilic cyclization of maleimide‐based enediynes that was initiated by bromide ions exhibited a previously unreported C2−C7 cyclization pattern.
Published Version
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