The hydrolysis of amides, esters, and related compounds in acid solution. Part IV. Phenyl chloroformate and the 1-(methoxycarbonyl)-imidazolium and -pyridinium ions

Abstract

The kinetics of hydrolysis of these three substrates in moderately concentrated solutions of H₂SO₄, HClO₄, and HCl has been studied. None of these reactions is acid catalysed. Medium effects are compared with those found in similar but acid-catalysed reactions. The reactivity of the cations, which serve as models for N-protonated carbamates, are compared with those of similar models for N-protonated amides, and in the light of the comparison the mechanism of hydrolysis of protonated carbamates is discussed.