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Hofmann-Martius rearrangementThe 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 [1] [2] Product highlightWhen the catalyst is a metal halide the reaction is also called the Reilly-Hickinbottom rearrangement [3]. 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 is applied to a 3-N(CH3)(C6H5)-2-oxindole [4] [5]:
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Hofmann-Martius_rearrangement". A list of authors is available in Wikipedia. |
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