Study of the mechanism of formation of symmetric bis-dibenziodolium salts: Substituent effects

CHED 450

Shauna M. Paradine, smp12@albion.edu, Stacy Capehart, slc13@albion.edu, William D Andert, and Andrew N. French, afrench@albion.edu. Department of Chemistry, Albion College, Albion, MI 49224
Hypervalent iodine compounds are versatile reagents that have found applications in a plethora of synthetically interesting organic transformations. Biaryliodonium salts, for example, are useful as arylating agents for nucleophiles and also have been found to be biologically active. However, dibenziodolium salts, their cyclic counterparts, have not been nearly so widely researched. These compounds have the potential to produce highly functionalized biphenyl systems and thus are a subject of interest. The research presented here seeks to study specifically the formation of bis-dibenziodolium triflates in the m-CPBA oxidation of symmetrically substituted diiodobiphenyls, in particular the types of effects that various substituents have on the formation of the bis- salts versus that of the corresponding mono- salts with iodine loss. This is accomplished through the synthesis of diiodobiphenyls from symmetrically-substituted para-biphenyls followed by application in the aforementioned oxidation reaction.