Esterification of unprotected sucrose with acid chlorides in aqueous medium: kinetic reactivity versus acyl- or alkyloxycarbonyl-group migrations

The study of the competition between formation, migration and hydrolysis of sucrose mono-esters and -carbonates confirmed that the pre-eminent reactivity of some secondary positions persists in aqueous medium, and in particular, OH-2, even though fast subsequent migrations finally enrich the mixture in compounds substituted at the primary positions. The reaction was also shown to depend strongly on the starting sucrose concentration providing higher substituted derivatives in the case of hydrophobic acylating agents, in contrast to smaller chains.