Synthesis of 1, 2-Bis (4'-Oxa-3', 5'-Dioxotricyclo-[4.3.0.1^{2, 5}] Decane-8'-Yloxy) Ethane Involving a Flexible Bridging Moiety by Combination of Heteropolyacids as Solid Acid Catalysts and 1, 4-Dioxane as a Bridging Reagent

Abstract

1, 2-Bis (4'-oxa-3', 5'-dioxotricyclo-[4.3.0.1^{2, 5}] decane-8'-yloxy) ethane (BNA), which is a candidate for a monomeric starting material of the soluble polyimide, has been synthesized from 5-norbornene-2, 3-dicarboxylic anhydride (NA) and 1, 4-dioxane (1, 4-DO) via solid acid catalysis over the heteropolyacids such as H₃PW₁₂O₄₀·30H₂O and H₄SiW₁₂O₄₀·30H₂O. In all the conditions without 1, 4-DO, no reaction occurs. Thus, it seems that this novel reaction contains an acid-catalyzed cleavage step of 1, 4-DO by the very strong acidity of the heteropolyacids. The target compound (BNA) can be obtained in satisfactory yields (-90%).