Effects of Counter Cations of Base Catalysts on Nitrosation Mechanisms

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概要

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• Reaction of 2-butanone(1)with tert-butyl nitrite(tert-BuONO)was performed using base catalysts(RO^-M^+:R=CH_3, C_2H_5;M^+=Li^+, Na^+, K^+)in alcohols(CH_3OH or C_2H_5OH). In this report, the effects of M^+ of RO^-M^+ on the nitrosation mechanisms were investigated. The yield of E-hydroxyimino compound(5E)increases much better in the reaction using Na^+ or K^+ as M^+ compared with that using Li^+. It is also observed that the yield of 5E increases by addition of crown ether as a cation-capturing agent. The experimental results suggested that under the conditions lowering the effects of M^+ of RO^-M^+ on the nitrosation mechanisms, because the reactivity of naked enolate of 1 increases and the reaction in the C-N bond formation process tends to proceed via open-chain transition state without M^+, the yield of 5E tends to increase.

• 公益社団法人日本薬学会の論文
• 2001-12-01

著者

• 池田 衡

  丸石製薬株式会社中央研究所

• 後藤 義久

  Faculty of Pharmaceutical Sciences Kanazawa University

• Niiya T

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Yukawa M

  Fukuoka Univ. Fukuoka Jpn

• Yukawa Miho

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Goto Yoshinobu

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Goto Yoshinobu

  Department Of Clinical Neurophysiology Graduate School Of Medical Sciences Neurological Institute Fa

• Niiya Tokihiro

  Faculty Of Pharmaceutical Sciences Fukuoka University

• IKEDA Hirohito

  Faculty of Pharmaceutical Sciences, Fukuoka University

• Ikeda Hirohito

  Faculty Of Pharmaceutical Sciences Fukuoka University

• Yukawa Miho

  Faculty Of Pharmaceutical Fukuoka University

• Ikeda Hirohito

  Faculty Of Pharmaceutical Fukuoka University

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