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Bioactive Heterocycles I pp 39–76Cite as

Manganese(III)-Based Peroxidation of Alkenes to Heterocycles

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Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 6))

Abstract

Synthesis of endoperoxides and hydroperoxides using tris(2,4-pentanedionato)manganese(III) or manganese(III) acetate is described. The reaction of various alkenes with tris(2,4-pentanedionato)manganese(III) at ambient temperature in air gives 4-acetyl -1,2-dioxan-3-ols. The manganese(III) acetate-catalyzed aerobic oxidation of various alkenes in the presence of various 1,3-dicarbonyl compounds also gives the corresponding 1,2-dioxan-3-ols. The basic skeleton of naturally occurring heterocycle-fused endoperoxides can be produced by the manganese(III)-catalyzed aerobic oxidation. On the other hand, a similar reaction using barbituric acids, pyrazolidinediones, and hydroxyquinolinones gives bis(hydroperoxyethyl) derivatives. In addition, the direct hydroperoxidation of the cyclic amides occurs in the absence of alkenes. The spectroscopic features, stereochemistry, mechanism for the formation of 1,2-dioxan-3-ols, and synthetic application are also mentioned.

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Acknowledgments

I gratefully acknowledge Professor Shoji Eguchi, Editor of Japan, Heterocyclic Communications, for giving me the chance to write this review. The research was supported by Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and also by Grants-in-Aid for Scientific Research from the Japan Society for the Promotion of Science.

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

    Hiroshi Nishino

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Correspondence to Hiroshi Nishino .

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Shoji Eguchi

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Nishino, H. Manganese(III)-Based Peroxidation of Alkenes to Heterocycles. In: Eguchi, S. (eds) Bioactive Heterocycles I. Topics in Heterocyclic Chemistry, vol 6. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_023

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