Simple route to azabicyclic peroxides from tetramic acid derivatives using manganese (III)-based molecular oxygen trapping reaction

FA Chowdhury, H Nishino…

Index: Chowdhury, Firoz Alam; Nishino, Hiroshi; Kurosawa, Kazu Heterocycles, 1999 , vol. 51, # 3 p. 575 - 591

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Citation Number: 25

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- ...