ChemInform Abstract: Derivatives of Naphthalene‐1,4,5,8‐tetracarboxylic Acid. Part 5. Reactions of Bisimides of Naphthalene‐1,4,5,8‐tetracarboxylic Acid with Alkali.

Abstract

The title compounds(I) are converted to the corresponding uncleaved sodium or potassium derivatives by gentle heating in the presence of NaOH or KOH, as is shown by the conversions of (Ia) and (Ic) to the corresponding compounds (IIa) and (IIb).

Molecular modelling of ring-opening polymerisation of lactamimide-containing macrocyclic esters

“…Strong hydrolysing reagents such as hot, concentrated sulfuric acid or KOH in tert-butyl alcohol are required for their saponification 1) . A completely different reaction pathway is observed, however, if, under much milder conditions, alkali metal hydroxides in alcohol react with six-membered bisimides such as naphthalene-1,8 : 4,5-tetracarboxylyc bisimides producing lactamimides 2) with loss of a C1 fragment from one carboximide. In all cases only one of the imide ring systems is transformed to lactam leaving the second one unchanged, and recently the mechanism of this rearrangement has been proposed 3) .…”