Publications by Year: 2007


The functionalization of deep-cavity cavitands via electrophilic substitution was investigated. In the parent structures, substitution occurs both at the exo position of the bowl-shaped hosts and on the convex face. Little or no endo substitution was observed. In contrast, derivatives in which methyl groups blocked the reaction sites on the convex face reacted selectively at the exo positions.
Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. C.; Ramamurthy, V. Photo-Fries reaction in water made selective with a capsule. Org. Biomol. Chem. 2007, 5, 236-238.
The water soluble capsule formed by a deep cavity cavitand with eight carboxylic acid groups controls product distribution during photo-Fries rearrangement of naphthyl esters in water by restricting the mobility of primary singletradical pair.