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Peri selectivity of the electrocyclization of 1-aryl- and heteroaryl-substituted (1Z,3Z)-1,3,5-hexatrienes, obtained by Ru-catalyzed linear coupling of 1,6-diynes to Z-propenyl(hetero)arenes, can be efficiently modulated depending on the aromaticity of the (hetero)arene: 1,3,5-hexatrienyl(hetero)arenes give 8pi e- electrocyclization with the exception of 1,3,5-hexatrienylbenzenes, which give 6pi e- electrocyclization.
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Garcia-Rubin et al. (2009) studied this question.
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