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Rearrangement Reactions

rearrangement reactions   Named Reactions in Organic Synthesis

Featured reactions:

 

A rearrangement reaction occurs when the carbon skeleton of a molecule is rearranged to provide a structural isomer of the original molecule. Frequently a substituent moves from one atom to another atom in the same molecule. Alongside substitution and addition reactions, rearrangements are of fundamental importance within organic synthesis.

One of the earliest named reactions featuring rearrangement is the Lossen rearrangement. In 1872 German chemist Wilhelm Lossen discovered that pyrolysis of benzoyl benzohydroxamate, formed by mixing phenylhydroxamic acid with benzoic acid, gave a mixture of phenyl isocyanate and benzoic acid. Ultimately the conversion of O-acyl hydroxamic acids to their corresponding isocyanates became known as the Lossen rearrangement.

The reaction is still popular today, as although it is closely related to both the Hofmann and Curtius rearrangements, it utilizes much milder reaction conditions and avoids the need to use potentially hazardous azides.

In this series, we feature the following rearrangement reactions:

 

Other named reactions that involve rearrangement of the carbon skeleton include:

  • Brook rearrangement
  • Carroll rearrangement
  • Ciamician–Dennstedt rearrangement
  • Cope rearrangement
  • Dimroth rearrangement
  • Favorskii rearrangement
  • Lossen rearrangement
  • Meisenheimer rearrangement
  • Overman rearrangement
  • Smiles rearrangement
  • Sommelet–Hauser rearrangement
  • Wittig rearrangement


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Other reaction categories:

Electrophilic aromatic substitution

Nucleophilic substitution reactions

Heterocycle-formation

Transition metal-catalyzed couplings

Oxidation

Reactions involving carbonyl compounds

Reduction reactions


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