o-またはP-クロロニトロベンゼンとナトリウムP-またはo-ニトロフェノラートとから2,4'-ジニトロジフェニルエーテル合成における4,4-および2,2-異性体の副生について

Synthesis of 2, 4'-dinitrodiphenyl ether (2, 4'-DNDPE), an intermediate of high-functional polymers, was carried out by the condensation of p- or o-chloronitrobenzene and sodium - or p-nitrophenolate in 1, 3 -dimethy1-2-imidazolidinone (dipolar aprotic solvent) at 1o40 and 180°C (Table 1 and Table 2). It shows that it is difficult to obtain 2, 4'-DNDPE selectively in high yield by this method due to by-production of 4, 4'- and 2, 2'-isomers. The results imply that the nucleophilic substitution occurs between dinitrodiphenyl ether and sodium nitrophenolate (Scheme 1).