Nucleophilic Ion Pairs. Facile Cleavage of an Amide Substrate by Hydroxamate Anions

An amide substrate(N-methyl-2,4-dinitroacetanilide) is readily cleaved by tetraethylammcnium hydroxamate ion pairs in dry, aprotic solvents at room temperature, and the reaction is efficiently suppressed by minute amounts of water. This is the first example of efficient nucleophilic catalysis of amide cleavage at ambient conditions.