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The Hofmann–Martius rearrangement in organic chemistry is a rearrangement reaction converting an N-alkylated aniline to the corresponding ortho and / or para aryl-alkylated aniline. The reaction requires heat, and the catalyst is an acid like hydrochloric acid. When the catalyst is a metal halide the reaction is also called the Reilly–Hickinbottom rearrangement. In one study this rearrangement was applied to a 3-N(CH3)(C6H5)-2-oxindole: The reaction is named after German chemists August Wilhelm von Hofmann and Carl Alexander von Martius.

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  • Die Hofmann-Martius-Umlagerung ist in der Chemie die säurekatalysierte Umlagerung von N-alkylierten Anilinderivaten zu den entsprechenden ortho- und para-alkylierten Anilinderivaten. Die Reaktion ist mechanistisch mit der Fries-Umlagerung verwandt. Praktisch wird hierzu in der Hitze mit einer anorganischen Säure, meist Salzsäure, gearbeitet. Die Umlagerungsreaktion ist nach ihren Entdeckern, den deutschen Chemikern August Wilhelm von Hofmann (1818–1892) und Carl Alexander von Martius (1838–1920) benannt. (de)
  • The Hofmann–Martius rearrangement in organic chemistry is a rearrangement reaction converting an N-alkylated aniline to the corresponding ortho and / or para aryl-alkylated aniline. The reaction requires heat, and the catalyst is an acid like hydrochloric acid. When the catalyst is a metal halide the reaction is also called the Reilly–Hickinbottom rearrangement. The reaction is also known to work for aryl ethers and two conceptually related reactions are the Fries rearrangement and the Fischer–Hepp rearrangement. Its reaction mechanism centers around dissociation of the reactant with the positively charged organic residue R attacking the aniline ring in a Friedel–Crafts alkylation. In one study this rearrangement was applied to a 3-N(CH3)(C6H5)-2-oxindole: The reaction is named after German chemists August Wilhelm von Hofmann and Carl Alexander von Martius. (en)
  • Penataan ulang Hofmann-Martius dalam kimia organik adalah reaksi penataan ulang yang mengubah anilina yang ter-N-alkilasi menjadi anilina yang teraril alkilasi pada posisi orto maupun para. Reaksi ini memerlukan panas dan katalis asam seperti asam klorida Ketika katalisnya merupakan logam halida, ia juga disebut sebagai penataan ulang Reilly-Hickinbottom. Reaksi ini juga dapat berjalan untuk aril eter. Dua reaksi yang berkaitan erat dengan reaksi ini adalah dan . Mekanisme reaksi ini berpusat pada disosiasi reaktan dengan residu organik bermuatan positif R yang menyerang cincin anilina pada alkilasi Friedel-Crafts. Pada satu kajian, penataan ulang ini diterapkan ke 3-N(CH3)(C6H5)-2-oksindola: (in)
  • Il riarrangiamento di Hofmann–Martius o reazione di Hofmann-Martius in chimica organica è una reazione di riarrangiamento che converte una N-alchilata anilina alla corrispondente e/o aril-alchilata anilina. La reazione richiede calore, e il catalizzatore è un acido come l'acido cloridrico. Il riarrangiamento di Hofmann–Martius Quando il catalizzatore è uno ioduro metallico allora viene anche detta riarrangiamento di Reilly–Hickinbottom. La reazione è nota anche per gli eteri arilici e due reazioni concettualmente correlate sono il e il riarrangiamento di Fischer-Hepp. (it)
  • Перегрупування Гофмана — Марціуса (рос. перегруппировка Гофмана — Марциуса, англ. Hofmann — Martius rearrangment) — термічне перетворення N-алкіланілінгідрохлоридів у о- і п-алкіланіліни. (uk)
  • 霍夫曼-马蒂乌斯重排反应(Hofmann-Martius rearrangement)以奥古斯特·威廉·冯·霍夫曼和二人命名。 酸(如盐酸)催化下,N-的苯胺衍生物在加热时发生重排,得到相应的邻/对烷基苯胺衍生物。 以金属卤化物催化时,反应亦称 Reilly-Hickinbottom 重排反应。 芳醚也可发生类似的重排。 (zh)
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  • Die Hofmann-Martius-Umlagerung ist in der Chemie die säurekatalysierte Umlagerung von N-alkylierten Anilinderivaten zu den entsprechenden ortho- und para-alkylierten Anilinderivaten. Die Reaktion ist mechanistisch mit der Fries-Umlagerung verwandt. Praktisch wird hierzu in der Hitze mit einer anorganischen Säure, meist Salzsäure, gearbeitet. Die Umlagerungsreaktion ist nach ihren Entdeckern, den deutschen Chemikern August Wilhelm von Hofmann (1818–1892) und Carl Alexander von Martius (1838–1920) benannt. (de)
  • Il riarrangiamento di Hofmann–Martius o reazione di Hofmann-Martius in chimica organica è una reazione di riarrangiamento che converte una N-alchilata anilina alla corrispondente e/o aril-alchilata anilina. La reazione richiede calore, e il catalizzatore è un acido come l'acido cloridrico. Il riarrangiamento di Hofmann–Martius Quando il catalizzatore è uno ioduro metallico allora viene anche detta riarrangiamento di Reilly–Hickinbottom. La reazione è nota anche per gli eteri arilici e due reazioni concettualmente correlate sono il e il riarrangiamento di Fischer-Hepp. (it)
  • Перегрупування Гофмана — Марціуса (рос. перегруппировка Гофмана — Марциуса, англ. Hofmann — Martius rearrangment) — термічне перетворення N-алкіланілінгідрохлоридів у о- і п-алкіланіліни. (uk)
  • 霍夫曼-马蒂乌斯重排反应(Hofmann-Martius rearrangement)以奥古斯特·威廉·冯·霍夫曼和二人命名。 酸(如盐酸)催化下,N-的苯胺衍生物在加热时发生重排,得到相应的邻/对烷基苯胺衍生物。 以金属卤化物催化时,反应亦称 Reilly-Hickinbottom 重排反应。 芳醚也可发生类似的重排。 (zh)
  • The Hofmann–Martius rearrangement in organic chemistry is a rearrangement reaction converting an N-alkylated aniline to the corresponding ortho and / or para aryl-alkylated aniline. The reaction requires heat, and the catalyst is an acid like hydrochloric acid. When the catalyst is a metal halide the reaction is also called the Reilly–Hickinbottom rearrangement. In one study this rearrangement was applied to a 3-N(CH3)(C6H5)-2-oxindole: The reaction is named after German chemists August Wilhelm von Hofmann and Carl Alexander von Martius. (en)
  • Penataan ulang Hofmann-Martius dalam kimia organik adalah reaksi penataan ulang yang mengubah anilina yang ter-N-alkilasi menjadi anilina yang teraril alkilasi pada posisi orto maupun para. Reaksi ini memerlukan panas dan katalis asam seperti asam klorida Ketika katalisnya merupakan logam halida, ia juga disebut sebagai penataan ulang Reilly-Hickinbottom. Pada satu kajian, penataan ulang ini diterapkan ke 3-N(CH3)(C6H5)-2-oksindola: (in)
rdfs:label
  • Hofmann-Martius-Umlagerung (de)
  • Penataan ulang Hofmann-Martius (in)
  • Hofmann–Martius rearrangement (en)
  • Riarrangiamento di Hofmann-Martius (it)
  • Перегрупування Гофмана — Марціуса (uk)
  • 霍夫曼-马蒂乌斯重排反应 (zh)
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