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Oxidation of aldimines to amides by m-CPBA and BF3ˇOEt2

Gwang-il An, Misoo Kim, Jin Yeon Kim and Hakjune Rhee*

*Department of Chemistry, Hanyang University, Ansan, Kyunggi-Do 425-791, Republic of Korea, Email: hrheehanyang.ac.kr

G. An, M. Kim, J. Y. Kim, H. Rhee, Tetrahedron Lett., 2003, 44, 2183-2186.

DOI: 10.1016/S0040-4039(03)00156-4

Abstract

Several amides were obtained in high yields by an efficient method from the corresponding imines which are readily prepared from aldehydes. This procedure involves the oxidation of aldimines with m-CPBA and BF3ˇOEt2. In this reaction, the product is strongly influenced by the electron releasing capacity of the aromatic substituent.

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Key Words

oxidative rearrangement, oxidation, aldimines, migratory aptitude, formamides, amides, MCPBA

ID: J72-Y2003-980