THE REACTION OF PYRIDINE AND PICOLINES WITH 2-BROMO-2-NITRO-1,3-INDANDIONE

Abstract

2-Bromo-2-nitro-1,3-indandione (I) reacts with pyridine in a complex reaction at ordinary temperature. The main reaction products are 2-nitro-1,3-indandione pyridine salt, pyridine hydrobromide, phthalic acid, and a black tar consisting of oxidized polymer of pyridine hydrobromide. The reaction of (I) with picolines follows the same route.The electronic theory has been applied to demonstrate the structure of 2-nitro-1,3-indandione (II). In water solutions or in salts (II) exists in the form of an anion which is stabilized by several resonating structures.