In organic chemistry, a sigmatropic reaction (from Greek τρόπος (trópos) 'turn') is a pericyclic reaction wherein the net result is one sigma bond (σ-bond)...

is an example of a [2,3]-sigmatropic reaction. The Stevens rearrangement is a [1,2]-rearrangement. A [3,3]-sigmatropic reaction has been observed in certain...

a pericyclic reaction is the type of organic reaction wherein the transition state of the molecule has a cyclic geometry, the reaction progresses in...

are sigmatropic reaction such as the Cope rearrangement. Cyclic rearrangements include cycloadditions and, more generally, pericyclic reactions, wherein...

meaning the reaction between these species is allowed as well. This is referred to as the "inverse electron demand Diels–Alder." A sigmatropic rearrangement...

ene reaction Shi epoxidation Shiina esterification Shiina macrolactonization or Shiina lactonization Sigmatropic reaction Simmons–Smith reaction Simonini...

[3,3]-sigmatropic reaction in the original report but call it a retro-ene reaction in another publication. (Note: The IUPAC defines a sigmatropic rearrangement...

formed from PCC can isomerize via a [3,3]-sigmatropic reaction and following oxidation yield an enone, in a reaction known as the Babler oxidation: This type...

ketene-imine cycloaddition Dyotropic reaction Electrocyclic reaction Group transfer reaction Sigmatropic reaction Polymerization Ring-opening metathesis...

resulting in higher yields for the reaction. The steric bulk of the ortho group assists in the [3,3]-sigmatropic rearrangement required for product formation...

final pyrrole is then formed by a [1,3] sigmatropic rearrangement. The Trofimov reaction is a powerful reaction for building pyrroles in total synthesis...

The Cope rearrangement is an extensively studied organic reaction involving the [3,3]-sigmatropic rearrangement of 1,5-dienes. It was developed by Arthur...

"exterior" lobes of the bond. The components of all pericyclic reactions, including sigmatropic reactions and cycloadditions, and electrocyclizations, can be classified...

2,3-Sigmatropic rearrangements are a type of sigmatropic rearrangements and can be classified into two types. Rearrangements of allylic sulfoxides, amine...

bond-forming chemical reaction discovered by Rainer Ludwig Claisen. The heating of an allyl vinyl ether will initiate a [3,3]-sigmatropic rearrangement to...

precipitated Étard complex. The Étard complex is then decomposed by a [2,3] sigmatropic rearrangement under reducing conditions to prevent further oxidation...

reaction that activates the C−H bond. The second step is a [2,3] sigmatropic reaction. Oxidations involving selenium dioxide are often carried out with...

puzzle in organic chemistry. The conversion is described as a [5,5]sigmatropic reaction. In terms of its physical properties, 4,4'-benzidine is poorly soluble...

thioethers to generate sulfur ylides, which can subsequently undergo a 2,3-sigmatropic rearrangement, and will not cyclopropanate an alkene in the same molecule...

by the trifluoroacetate anion. This sets the molecule up for a [3.3]-sigmatropic rearrangement which furnishes the trifluoroacetylated methylpyridine...

electrocyclic reaction, followed by two suprafacial 1,5-sigmatropic hydrogen shifts, as shown below. An often studied electrocyclic reaction is the conrotatory...

developments. The reaction allows the formation of allylic alcohols from allylic sulfoxides in a 2,3-sigmatropic rearrangement. The reaction is a powerful...

with bimolecular reaction kinetics by an intermolecular free radical reaction. The intramolecular isomerisation, a 1,3-sigmatropic reaction, is unfavorable...

phenylhydrazone 1 to the intermediate 2. Subsequently, a heat-induced sigmatropic reaction occurs to produce 3, which is protonated and cyclizes into 4. Elimination...

migrate. It is a reaction involving j + 1 electrons: j − 1 from the π-system and 2 from σ-bond. Using FMO analysis, [1,j]-sigmatropic rearrangements are...

in cascade transformations, pericyclic reactions include cycloadditions, electrocyclic reactions and sigmatropic rearrangements. Although some of the abovementioned...

a nucleophilic displacement of chloride by the azide ion. A (3,3)Sigmatropic reaction takes place between the azide and the alkyne to the allenyl azide...

chlorochromate by the allylic alcohol. The ester then undergoes a [3,3]-sigmatropic shift to create the isomeric chromate ester (2). Finally, oxidation of...

uncracked dimer. The hydrogen atoms in cyclopentadiene undergo rapid [1,5]-sigmatropic shifts. The hydride shift is, however, sufficiently slow at 0 °C to allow...

carbonyl compounds by a mechanism typical for such a [3,3]-sigmatropic rearrangement. The reaction is highly general: a wide variety of precursors undergo...