Green and selective iodination of diamondoid adamantane by β-cyclodextrin as a molecular reactor

Abstract

β-Cyclodextrin (β-CD) is a versatile and naturally occurring host which strongly binds adamantane and its derivatives. Based on this binding, we prepared a host–guest inclusion complex of β-CD with adamantane, and selectively iodinated the included adamantane to 1-iodoadamantane by iodoform. The only formed monoiodo product confirmed our initial assumption that three out of the four methine groups of the guest adamantane are shielded when adamantane is included into the cavity of β-CD and, therefore, iodination just takes places on the methine group directing to the outside of the cavity of β-CD.