Welcome to the Named Reactions category, where we explore the significant transformations in organic chemistry that bear the names of renowned chemists. Dive into the rich history and fundamental mechanisms behind reactions such as the Grignard reaction, Diels-Alder reaction, and Heck reaction, among others. Uncover the applications, limitations, and synthetic utility of these named reactions in organic synthesis. Discover how these reactions have shaped the field of organic chemistry and continue to inspire innovation. Embark on a journey through the world of named reactions and unlock the secrets of their chemical transformations.
What is HERON rearrangement? The HERON rearrangement, which stands for HEteroatom Rearrangements On Nitrogen, is a chemical reaction that involves the migration of oxygen from the nitrogen atom to the carbonyl carbon in bisheteroatom-substituted amides. This reaction leads to the formation of esters and 1,1-diazenes. Additionally, analogues of N,N’-diacyl-N,N’-dialkoxyhydrazines undergo thermal decomposition, which involves two … Read more
What is Meyer-Schuster rearrangement? The Meyer-Schuster rearrangement is a reaction that is catalyzed by acid and involves the rearrangement of secondary and tertiary α-acetylenic alcohols to α,β-unsaturated carbonyl compounds. The Meyer-Schuster rearrangement leads to the formation of aldehydes when the acetylenic group is terminal, and ketones when it is internal. In 1926, a rearrangement closely related … Read more
What is Fritsch-Buttenberg-Wiechell rearrangement? The Fritsch-Buttenberg-Wiechell rearrangement is a chemical reaction that involves the carbene-mediated rearrangement of 1,1-diaryl-2-haloethylenes to form diaryl acetylenes. References Fritsch, P. (1894), IV. Ueber die Darstellung von Diphenylacetaldehyd und eine neue Synthese von Tolanderivaten. [IV. On the preparation of diphenylacetaldehyde and a new synthesis of tolan derivatives.] Justus Liebigs Ann. Chem., … Read more
What is Gabriel-Colman rearrangement? The Gabriel-Colman rearrangement, also known as the Gabriel isoquinoline synthesis, or phthalimidoacetic ester → isoquinoline rearrangement, is a reaction first reported in 1900 by Gabriel and Colman. This reaction involves the rearrangement of alkyl phthalimidoacetate to form isoquinoline derivatives (or substituted benzothiazines) using alkoxide treatment. However, it is limited to phthalimido derivatives … Read more
What is Hayashi rearrangement? The Hayashi rearrangement is a chemical reaction that occurs when o-benzoylbenzoic acids are exposed to either sulfuric acid or phosphorous pentoxide. During this reaction, the molecular structure of the substrate undergoes a rearrangement, resulting in the formation of a new product. References M. Hayashi, “CCCXXXVI.—A new isomerism of halogenohydroxybenzoyltoluic acids” J. … Read more
What is Dimroth rearrangement? The Dimroth rearrangement is a reaction first described by Dimroth in 1909 that involves the base-catalyzed translocation of exo– and endo-cyclic heteroatoms on a heterocyclic ring. This reaction is commonly referred to as the Dimroth rearrangement or the Dimroth-type rearrangement, and it is also known as the Dimroth reaction in some … Read more
What is Fischer-Hepp rearrangement? The Fischer-Hepp rearrangement, which is also known as the nitrosamine rearrangement, is a chemical reaction that results in the rearrangement of secondary aromatic nitrosamines to form p-nitrosoarylamines. References Fischer, O. and Hepp, E. (1886), Zur Kenntniss der Nitrosamine. [On the knowledge of nitrosamines.] Ber. Dtsch. Chem. Ges., 19: 2991-2995. https://doi.org/10.1002/cber.188601902297
What is Hofmann-Löffler reaction? The Hofmann-Löffler reaction, also referred to as the Hofmann-Löffler-Freytag reaction, is a chemical process that leads to the formation of pyrrolidines or piperidines. This reaction is triggered by the thermal or photochemical decomposition of protonated N-haloamines. References Hofmann, A.W. (1883), Ueber die Einwirkung des Broms in alkalischer Lösung auf die Amine. … Read more
Whis is Chapman rearrangement? Mumm et al. reported the occurrence of a reaction in 1915, which was subsequently studied extensively by Chapman in the 1920s and 1930s. This reaction involves the thermal rearrangement of aryl imidates into N,N-diaryl amides and is commonly known as the Chapman rearrangement. It is occasionally referred to as the Beckmann-Chapman … Read more
What is Cornforth rearrangement? The Cornforth rearrangement refers to a chemical reaction where 4-carbonyl substituted oxazoles undergo thermal rearrangement, resulting in the formation of isomeric oxazoles through the use of dicarbonyl nitrile ylides. References J. W. Cornforth, The chemistry of penicillin. Clarke H.T., Johnson J.R., and Robinson R. (eds) Princeton University Press, New Jersey, 1949, … Read more
