After thiophene and furan were treated with n‐BuLi, respectively, the mixtures were reacted with various ketones and then dehydrated under acidic conditions. This reaction sequence led to the formation of 1‐(2‐heteroaryl)cycloalkenes and (2‐heteroaryl)alkenes. When the alkenes were treated with 10 mol % NIS, calix[4]arenes were produced as the major products, with minor amounts of calix[6]arenes sometimes being produced. Reducing the loading of NIS to 1 mol % and increasing its overall concentration to 6 M resulted in a substantial increase in the yield of hexaspirocyclohexyl calix[6]thiophene (from 2 to 66 %).
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