Synthesis of 2,8-dioxaspiro[4.5]decane-1,3,7,9-tetrone and the Reactions with amines

Article abstract of DOI:10.1246/bcsj.72.1075

For the studies of highly-sophisticated utilization of itaconic anhydride, some compounds of polybasic carboxylic acids having a quaternary or a spiro carbon atom were prepared, starting from itaconic anhydride and isoprene. Aliphatic tetracarboxylic dianhydride having a spiro carbon atom with five- and six-membered rings, 2,8-dioxaspiro[4.5]decane-1,3, 7,9- tetrone (TCDA), was also obtained. The reaction of TCDA with primary amines and subsequent dehydration gave two types of products, either diimides or imide (with five-membered ring)-anhydrides (with six-membered ring), depending on the hydrocarbon moiety of the amines used. It was suggested that each imide-anhydride was formed by the intramolecular ring transformation of the intermediate amic acid-anhydride.