The reactivity of organophosphorus compounds. Part XXVI. A kinetic study of reactions of o-dinitrobenzene with triethyl phosphite and diethyl methylphosphonite

Abstract

The occurrence of bimolecular nucleophilic aromatic substitution has been established in the reaction of o-dinitro-benzene with triethyl phosphite and diethyl methylphosphonite in acetonitrile solution. The role of the o-nitro-group in facilitating the nucleophilic substitution has been discussed in terms of ‘built-in solvation’ of the reaction centres. The exclusive formation of ethyl nitrite in the reactions has been shown to be compatible with the dealkylation of a quasi-phosphonium intermediate by nitrite ions.