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Cycloaromatization of Enediyne Compounds under the Action of Bromide Ions: Diradical/Zwitterionic/Anionic Pathways
Author(s) -
Chen Shudan,
Huang Shuai,
Wang Chonggang,
Ding Yun,
Hu Aiguo
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700136
Subject(s) - chemistry , diradical , enediyne , bromide , nucleophile , halide , medicinal chemistry , reactivity (psychology) , combinatorial chemistry , photochemistry , stereochemistry , organic chemistry , singlet state , catalysis , medicine , physics , alternative medicine , pathology , nuclear physics , excited state
Cycloaromatization 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.