Manganese (III) Acetate-Catalyzed Oxidation of 4-Piperidone-3-carboxylates in the Presence of 1,1-Disubstituted Alkenes

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概要

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• The manganese(III) acetate-catalyzed cycloperoxidation of 4-piperidone-3-carboxylates with 1,1-disubstituted alkenes is described. The 4-piperidone-3-carboxylates reacted with 1,1-disubstituted alkenes in the presence of a catalytic amount of manganese(III) acetate in air at 23 ℃ to give 1-hydroxy-8-aza-2,3-dioxabicyclo[4.4.0]-decane-6-carboxylates in good to moderate yields. The crystal structure of the azabicyclic peroxides was determined by an X-ray single crystal analysis. The oxidation of the 4-piperidone-3-carboxylates with 1,1-diphenylethene using a stoichiometric amount of manganese(III) acetate gave ethenyl- and ethyl-substituted 4-piperidones and 6-hydroxy-3-aza-7-oxabicyclo[4.3.0]nonane-1-carboxylate which was the same as the product obtained from the hydrogenolysis of the 1-hydroxy-8-aza-2,3-dioxabicyclo[4.4.0]decane-6-carboxylate.

• 熊本大学の論文

著者

• Nishino Hiroshi

  Department Of Applied Chemistry National Defense Academy

• Kumabe Ryoko

  Department of Materials and Life Science, Graduate School of Science and Technology, Kumamoto University

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