ChemInform Abstract: Unusual Example of Nucleophilic Substitution in Nitrophthalimide Series.

Abstract

carboxylic amidescarboxylic amides (benzene compounds) Q 0490 -097Unusual Example of Nucleophilic Substitution in Nitrophthalimide Series.-The reaction of 3-(I) and 4-nitrophthalimides (III) with hydroxylamine is studied. While 4-nitrophthalimide (III) undergoes amination in both the neighboring positions relative to the nitro group affording a mixture of the regioisomers (IV) and (V), the 3-nitro analogue (I) affords unexpectedly the 3,6-dihydroxyphthalimide (II). A possible reaction mechanism that explains this unexpected substitution is given. -(KUDRIK, E. V.; ZHARNIKOVA, M. A.; DERYABKINA, E. A.; SHAPOSHNIKOV, G. P.; Izv.