Reactivity of [bis(1-adamantylcarbonyloxy)iodo]arenes in substitution and addition reactions

The reactivity of [bis(1-adamantylcarbonyloxy)iodo]arenes with 4-methylquinoline (substitution) as a typical heteroaromatic base and phenyl vinyl sulfone (addition) as a typical activated olefin has been studied under thermal and irradiation conditions. The results suggest that electron-withdrawing groups on the aromatic ring in [bis(1-adamantylcarbonyloxy)iodo]arenes are detrimental to reactions. The crystal structures of [bis(1-adamantylcarbonyloxy)iodo]arenes 1b and 1e are reported.