V2EX beckmann rearrangement

Beckmann Rearrangement

定义 Definition

贝克曼重排:一种有机反应,通常在酸性条件下使肟(oxime)发生重排,生成酰胺(amide);若底物为环酮肟,常生成内酰胺(lactam)。该反应的关键特征是:与离去基团反式(anti)的取代基发生迁移。(该术语在有机化学中最常用;“rearrangement”本身还有更广义的“重排反应”含义。)

发音 Pronunciation (IPA)

/bkmn rrndmnt/

例句 Examples

The Beckmann rearrangement converts cyclohexanone oxime into caprolactam.
贝克曼重排可以把环己酮肟转化为己内酰胺。

Under strongly acidic conditions, the Beckmann rearrangement proceeds via activation of the oxime and migration of the anti substituent to form an amide.
在强酸条件下,贝克曼重排通常通过肟的活化并伴随反式取代基迁移来生成酰胺。

词源 Etymology

“Beckmann”来自德国化学家恩斯特奥托贝克曼(Ernst Otto Beckmann)的姓氏,该反应用他的名字命名;“rearrangement”意为“(分子内部)重排”,指原子/基团在分子内重新连接形成新结构的过程。

文学与著作中的用例 Literary Works

  • March’s Advanced Organic Chemistry(March 高等有机化学,机理与反应汇编类经典教材中常见条目)
  • Organic Chemistry(Clayden, Greeves & Warren,常用于讲解肟到酰胺/内酰胺的重排机理)
  • Advanced Organic Chemistry(Carey & Sundberg,涉及重排反应与立体化学要点)
  • Organic Syntheses(有机合成文献集,收录含贝克曼重排步骤的制备实例)
  • HoubenWeyl Methods of Organic Chemistry(有机合成方法学大型丛书,常在“重排/酰胺化”章节出现)
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