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 reactiv ity of some secondary positions persists in aqueous medium, and ill particu lar, OH-2, even though fast subsequent migrations finally enrich the mixtur e in compounds substituted at the primary positions. The reaction was also shown to depend strongly on the starting sucrose concentration providing hi gher substituted derivatives in the case of hydrophobic acylating agents, i n contrast to smaller chains. (C) 1999 Elsevier Science Ltd. All rights res erved.