MN(III)-BASED REACTION OF ALKENES WITH PYRROLIDINEDIONE DERIVATIVES -FORMATION OF BICYCLIC PEROXIDES AND THE RELATED-COMPOUNDS

Alkenes (1) and 2,3-pyrrolidinediones (2) were treated with manganese( III) acetate in acetic acid at 23 degrees C under a stream of dry air giving -hydroxy-8-aza-2,3-dioxabicyclo[4.3.0]nonan-9-ones (3) in good yields. The reaction at elevated temperature gave 4-ethenyl-2,3-pyrrol idinediones (6) and/or 4-alkyl-2,3-pyrrolidinediones (7) in good yield s. A wide variety of 2,3-pyrrolidinediones having an alkoxycarbonyl, c yano, or acyl group at the 4-position were tested to delineate the sco pe and limitations of these reactions. The mechanisms for the formatio n of the products were also discussed.