When quaternary ammonium hydroxide is heated to around 100°C, one of the C-N bonds breaks, producing an alkene, a tertiary amine, and water (Hoffmann decomposition). In this reaction, if there is a possibility that two or more alkenes are produced, the empirical rule is that the alkene with fewer substituents is more likely to be produced. If an ethyl group is included, ethylene is most likely to be produced. This general rule was discovered in 1851 by A. W. von Hoffmann of Germany. (Chemical formula) A similar tendency regarding the direction of the elimination reaction is also observed in the decomposition of sulfonium salts [R 3 S + ]X - . Source: Heibonsha World Encyclopedia, 2nd Edition Information |
水酸化第四アンモニウムを100℃くらいに加熱すると,C-N結合の一つが切れて,アルケンと第三アミンおよび水が生成する(ホフマン分解)。この反応において,2種以上のアルケンが生成する可能性がある場合には,置換基の少ないアルケンがより生成しやすいという経験則。もしエチル基が含まれるなら,エチレンが最も生成しやすいことになる。この通則は1851年ドイツのA.W.vonホフマンにより見いだされた。(化学式)脱離反応の方向に関する同様の傾向はスルホニウム塩[R3S+]X-の分解でも認められる。
出典 株式会社平凡社世界大百科事典 第2版について 情報 |
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