Synthesis of 4,4-bis(2-hydroperoxyalkyl)pyrazolidine-3,5-diones using manganese(III)-catalyzed autoxidation |
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Authors: | MdTaifur RahmanHiroshi Nishino Chang-Yi Qian |
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Institution: | a Department of Materials and Life Science, Graduate School of Science and Technology, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan b Department of Chemistry, Faculty of Science, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan |
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Abstract: | The autoxidation of a mixture of 1,2-disubstituted pyrazolidine-3,5-diones 1 and alkenes 2 in the presence of a catalytic amount of manganese(III) acetate dihydrate in air gave 4,4-bis(2-hydroperoxyalkyl)pyrazolidine-3,5-diones 3 in 75-96% yields. The structure of the bis(2-hydroperoxyethyl)pyrazolidine-3,5-dione 3 (R1=R2=Ph, R3=R4=4-FC6H4) has been corroborated by an X-ray single crystallographic analysis. On the other hand, the manganese(III) acetate oxidation of a mixture of 1 (R1=R2=Ph) and 2 (R3=R4=Ph) at elevated temperature gave 4,4-bis(2,2-diphenylethenyl)-1,2-diphenylpyrazolidine-3,5-dione (4) in good yield. |
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