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■ Mn(III)-based Reaction of Alkenes with Pyrrolidinedione Derivatives. Formation of Bicyclic Peroxides and the Related Compounds

Van-Ha Nguyen, Hiroshi Nishino,* and Kazu Kurosawa

*Department of Chemistry, Faculty of Science, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan

Abstract

Alkenes (1) and 2,3-pyrrolidinediones (2) were treated with manganese (III) acetate in acetic acid at 23 °C under a stream of dry air giving 1-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-pyrrolidinediones (6) and/or 4-alkyl-2,3-pyrrolidinediones (7) in good yields. A wide variety of 2,3-pyrrolidinediones having an alkoxycarbonyl, cyano, or acyl group at the 4-position were tested to delineate the scope and iminations of these reactions. The mechanisms for the formation of the products were also discussed.