The stabilities of Meisenheimer complexes. Part 31. The reactions of 2,2′,4,4′,6,6′-hexanitrostilbene with alkoxides

Abstract

¹ H N.m.r. and visible spectral measurements indicate three types of 1 : 1 interaction of 2,2′,4,4′,6,6′-hexanitrostilbene with alkoxides. σ-Adducts are formed by attack at the 3- or 1-ring position, while the third interaction may involve attack at the olefinic double bond. A 1 : 2 adduct is produced by attack at the 1- and 1′-ring position. Kinetic and equilibrium results for reactions with methoxide ions in methanol and ethoxide ions in ethanol have been obtained and are compared with those for related compounds.