Effect of metal ions in organic synthesis. Part XIII. Selective regeneration of hydroxyl and carboxyl groups from some derivatives by copper (II) ion-promoted hydrolysis

Abstract

Acetyl derivatives of alcoholic and phenolic hydroxyl groups represent not only useful educts, intermediates and products in organic, bioorganic and pharmaceutical chemistry, but also interesting derivatives for isolation, purification and characterization of alcohols and phenols (especially for natural products). Furthermore, the acetylation reaction is frequently used for the protection of hydroxyl function. In general, however, acetoxy-groups may be highly resistent to hydrolysis so that their conversion into hydroxyl groups often requires strongly basic or acidic media, expensive and/or hardly available reagents, complicated procedures. These conditions may be incompatible with sensitive substrates or with other insufficiently stable groups present in the molecular residue.^1,2 Very similar arguments are sound for some hydrazide derivatives of carboxylic acids.^1,3,4