Hofmann-Martius rearrangement

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


 * [[Image:Hofmann-MartiusRearrangement.png|400px|The Hofmann-Martius Rearrangement]]

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 is applied to a 3-N(CH3)(C6H5)-2-oxindole :


 * [[Image:Hofmann-MartiusApplication.png|400px|Hofmann-Martius Rearrangement of 3-N-Aryl-2-oxindoles ]]