Intramolecular Catalysis of Hydrolytic Reactions. II. The Hydrolysis of Phthalamic Acid^1,2

Abstract

Vol. SO filtered, washed, dried and weighed, following the procedure described by Iddles.12 The results are included in Table III.Three of the 2,4-dinitrophenylhydrazones are new:(1)2,4-dinitrophenylhydrazone of ^-carbethoxybenzaldehyde,

Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

“…The second is considered to consist of intramolecular catalysis, by the new N-methylamido function, of the hydrolysis or aminolysis of the second phthalamido bond. Most studies of intramolecular catalysis of amide hydrolysis (4) have been performed under acidic conditions and are not directly applicable to the present system. However, mechanisms for intramolecular catalysis under neutral and alkaline conditions d o exist (29,30).…”

Modification of ϵ‐amino group of lysine in proteins by acylation with pyromellitic dianhydride and o‐sulphobenzoic anhydride

“…Further, the modification is reversible since the modifying groups can be easily cleaved by hydrolysis which is facilitated by neighbouring group participation (cf. hydrolysis of phthalamic acid which is well known intramolecular process [20]). …”

Synthesis of aromatic polyimides from dianhydrides and diamines

“…As discussed earlier, it can cyclise intramolecularly to regenerate the anhydride, or it can cyclise to give isoimide or imide moieties. Although the carboxamide linkage is theoretically susceptible to direct hydrolysis, such a process has been shown to be 10 5 times slower than hydrolysis via an anhydride intermediate [40]. The probability that the group undergoes exchange reactions with amine impurities in the solvent or transamidation reactions with the solvent is also low under the conditions used.…”