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Paper | Regular issue | Vol 51, No. 3, 1999, pp.575-591
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8417
Simple Route to Azabicyclic Peroxides from Tetramic Acid Derivatives Using Manganese(III)-based Molecular Oxygen Trapping Reaction

Firoz Alam Chowdhury, Hiroshi Nishino,* and Kazu Kurosawa

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

Abstract

A simple one-step synthesis of azabicyclic peroxides was achieved by the manganese(III)-mediated oxidative formal [2+2+2] cycloaddition. The reaction of alkenes (1) with pyrrolidinediones (2) was carried out with manganese(III) acetate in acetic acid at 23 °C under a dry air stream to give 1-hydroxy-8-aza-2,3-dioxabicyclo[4.3.0]nonan-7-ones (3) in good to quantitative yields. Similar reactions at elevated temperature gave 3-ethyl-2,4-pyrrolidinediones (4) and/or 3-ethenyl-2,4-pyrrolidinediones (5) in good yields.