13C nuclear magnetic resonance of Jackson–Meisenheimer (σ-anionic)-type products formed when 1,3,5-trinitrobenzene, and when 2,4,6-trinitrotoluene, are dissolved in liquid ammonia

Abstract

1 : 1 and 2 : 1 products formed by nucleophilic attack of ammonia in liquid ammonia solutions of 1,3,5-trinitrobenzene and of 2,4,6-trinitrotoluene have been observed by ¹³C n.m.r. spectroscopy. In the latter reaction three 2 : 1 products are observed: two geometrical isomers formed by attack at the 1- and 3-position of 2,4,6-trinitrotoluene and a structural isomer formed by attack at the 3- and 5-position.