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Rearrangement Reactions

Rearrangements in chemistry: reactions and mechanisms.


In chemistry a rearrangement is a chemical reaction in which the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule.

The rearrangement is - like the substitution reaction and the addition reaction - one of the basic operations of chemical synthesis. Specific reaction types are listed under the heading of name reactions.

Below you will find short descriptions and online available information resources about rearrangement reactions and mechanisms in chemistry

Content, Topics

Lecture Notes, Tutorials

Anionic Rearrangements
Rearrangements induced by bases or electron rich sites. Virtual Textbook of Organic Chemistry

Carbocation Rearrangements
Here, a carbocation moves within a molecule to adopt a more stable state

Cationic Rearrangements
Rearrangements induced by cationic or electron deficient sites. Virtual Textbook of Organic Chemistry

Introduction to Rearrangement Reactions
Lecture notes

Rearrangement Reactions
Lecture notes

Rearrangement Reactions
Applied organic chemistry: reaction mechanisms and experimental procedures - Format: PDF

Partial Information

Achmatowicz Rearrangement
Conversion of furans to dihydropyrans

Amadori rearrangement
Animated slide show. Pudue University, USA - Format: PPT

Baeyer-Villiger Rearrangement
Formation of esters by reaction of ketones with percarboxylic acids. Organic Chemistry Portal

Baker-Venkataraman Rearrangement
An intramolecular variant of the Allan-Robinson reaction used in the synthesis of 1,3-diketone substituted derivatives of phenol from acylated phenols. Organic Chemistry Portal

Beckmann Rearrangement
Description of the reaction and detail at the mechanism. Organic Chemistry Portal

Beckmann Rearrangement
A rearrangement reaction of ketoximes or aldoximes for the synthesis of carboxamides

Benzidine Rearrangement
Benzidine synthesis by reduction of azobenzene with ammonium sulfide via hydrazobenzene as an intermediate

Benzilic Acid Rearrangement
A reaction of 1,2-diketones to form α-hydroxycarboxylic acids in the presence of strong bases such as potassium hydroxide. Organic Chemistry Portal

Brook Rearrangement
Bei dieser chemischen Reaktion findet eine intramolekulare Wanderung einer Silylgruppe von einem Kohlenstoffatom zu einem Sauerstoffatom statt. Organic Chemistry Portal

Claisen Rearrangement
This is a [3,3]-sigmatropic rearrangement of allyl vinyl ethers to γ,δ-unsaturated carbonyl compounds. Organic Chemistry Portal

Claisen Rearrangement
Description and reaction mechanism

Claisen-Eschenmoser Rearrangement
A Practical Variant of the Claisen-Eschenmoser Rearrangement: Synthesis of Unsaturated Morpholine Amides

Cope Rearrangement
The first discovered solid-phase synthesis, which is a reversible thermal isomerization of 1,5-dienes. The organic chemical reaction is one of the pericyclic reactions and is a sigmatropic [3,3] rearrangement. Organic Chemistry Portal

Cope Rearrangement
Description and reaction mechanism

Curtius Rearrangement
Description of the reaction and detail at the mechanism. Organic Chemistry Portal

Curtius Rearrangement
Also known as the curtius reaction or curtius degradation, a chemical reaction that occurs when carboxylic acid azides are heated. The conversion is primarily used to break down carboxylic acids to primary amines. In detail, a carboxylic acid azide is reacted with water via the intermediate stage of the isocyanate to form the primary amine. Depending on the reaction conditions, isocyanates, carbamates or urea derivatives can also be formed

Dakin-West Reaction
A chemical reaction to convert α-amino acids into α-acetamido-ketones using acetic anhydride and a base

Diaza-Cope Rearrangement
A heteroatomic variant of the Cope rearrangement. It is a [3,3]-sigmatropic rearrangement in chemical compounds from the imine group of substances, which have a 2,5-diazahexa-1,5-diene structural element

Favorskii Rearrangement
The Faworski rearrangement reaction basically describes the reaction of enolizable α-haloketones to form carboxylic acids with the addition of hydroxides. By varying the strong base used, carboxylic acid esters and carboxylic acid amides are also accessible. Organic Chemistry Portal

Fries Rearrangement
This reaction describes the electrophilic rearrangement of aryl esters under Lewis acid catalysis to the corresponding aryl ketone. Organic Chemistry Portal

Heyns Rearrangement
A chemical reaction in which the amino groups of an amino acid readily add as nucleophilic compounds to the carbonyl function of reducing sugars. The reaction of a ketosis leads via the rearrangement to the corresponding aminoaldose, which is also referred to as a Heyns compound. This transformation also occurs in the initial phase of the Maillard reaction. The corresponding reaction of an aldose to an aminoketose is called the Amadori rearrangement - Format: PDF

Hofmann Rearrangement
Also known as Hofmann degradation, a chemical reaction in which an unsubstituted carboxamide is reacted with bromine in the presence of a base in water. This results in an amine shortened by a carbonyl group

Ireland-Claisen Rearrangement
Description of the reaction and detail at the mechanism. Organic Chemistry Portal

Johnson-Claisen Rearrangement
In this chemical reaction, an orthoester is converted to an ester with an allyl alcohol via an acetal

Lobry-de Bruyn-van Ekenstein transformation
Also known as Lobry de Bruyn-Alberda van Ekenstein chemical reaction, which is a special case of ketol-enediol tautomerism. It is an acid- or base-catalyzed aldose-ketose isomerization. The reaction is important, among other things, for the industrial synthesis of ketoses. Wiki

Newman-Kwart Rearrangement
In the NKR a intramolecular aryl migration of O-thiocarbamates at high temperatures leads to S-thiocarbamates. Organic Chemistry Portal

Overman Rearrangement
An N-allylamide is formed by reacting an allyl alcohol with sodium hydride and trichloroacetonitrile. The Overman reaction is a variant of the Claisen rearrangement. Organic Chemistry Portal

Pinacol Rearrangement
Di-tert-glycols react to form α-tertiary ketones under the action of a protonic acid. Organic Chemistry Portal

Pummerer Rearrangement
The Sulfinate-Sulfone Pummerer Rearrangement - Format: PDF

Schmidt Rearrangement
The acid-catalyzed chemical reaction of hydrazoic acid with carboxylic acids leads to amines, cyanides, amides or imines via rearrangement and elimination of N2. Organic Chemistry Portal

Stevens Rearrangement
Under the action of a base, an organic radical R (alkyl, allyl, benzyl) is shifted from a tetra-bonded nitrogen atom (a quaternary ammonium ion) to an adjacent carbon atom. Organic Chemistry Portal

Wagner-Meerwein Rearrangement
This is an acid-catalyzed, nucleophilic [1,2] rearrangement of the carbon skeleton via carbenium ions

Wittig Rearrangement
[1,2]- and [2,3]-Wittig Rearrangement - Format: PDF

Wittig: [1,2]-Wittig Rearrangement
An ether reacts chemically with an organolithium compound to form an alcohol. Organic Chemistry Portal

Wittig: [2,3]-Wittig Rearrangement
Conversion of an allyl ether into a homoallylic alcohol through a concerted pericyclic process. Organic Chemistry Portal

Wolff Rearrangement
The thermal or photochemical conversion of α-diazoketones into ketenes. Organic Chemistry Portal

Special Information

Allylsilane Rearrangement
Mechanistic Studies - Format: PDF


Last update: 31.10.2022

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