過酸化ニッケルによる酸化反応(第9報)アルデヒドのAmmonoxidationによる酸アミドの合成

概要

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Some kinds of amides can be obtained in a good yield by a liquid-phase ammonoxidation of aldehydes in ether at -20° to -25° with nickel peroxide. Benzylic and allylic alcohols were also effectively converted into the corresponding amides in a similar way. The reaction proceeds by hydrogen abstraction from the intermediate, α-amino-alcohol, which is in equilibrium with aldehyde and ammonia. Nickel peroxide is considered to be the only effective oxidant in this reaction. The substituent effect on the reaction rates of benzaldehyde derivatives was examined and it was found that the reaction rate decreased in the order of m-nitrobenzaldehyde, benzaldehyde, and p-methoxybenzaldehyde, which was attributed to the increasing equilibrium concentration of the corresponding α-amino-alcohol, and the rate of hydrogen abstraction from α-amino-alcohols was hardely affected by substituents.
公益社団法人日本薬学会の論文
1975-10-25