Topographical nature of the polymer matrix and reactivity of attached functional groups: effect of crosslink density on the efficiency of solid-phase hypochlorite oxidations

Abstract

A series of crosslinked polystyrene-supported hypohalite reagents with the reagent function in different microenvironments were prepared and their reactivities in oxidation and halogenation reactions on organic substrates were investigated. The reactivity of the hypohalite reagent function was observed to be dependent on the topographical nature of the polymer matrix. The reactivity in these cases depends on the degree of crosslinking which affects the extent of functionalisation and also the mechanical integrity and stability of the polymer support. Hypohalite reagents starting from 1%, 2%, 4% and 20% crosslinked polystyrenes were prepared and used for oxidation and halogenation reactions. The reactivity of the hypohalite function is reduced considerably when the degree of crosslinking is increased. A decrease in the degree of functionalisation is also observed with increase in the degree of crosslinking.