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 Schmidt reaction? The Schmidt reaction, also known as the Schmidt rearrangement, is a chemical reaction that involves the addition of hydrazoic acid to carboxylic acids, aldehydes, and ketones under acidic conditions. The products of this reaction are amines, nitriles, and amides, respectively. During the Schmidt reaction, tertiary alcohols and substituted alkenes undergo a … Read more
What is retropinacol rearrangement? The retropinacol rearrangement refers to a chemical process that occurs under acidic conditions, whereby an alcohol molecule is transformed into a rearranged olefin compound. References N. Zelinsky, J. Zelikow, “Über Umwandlung von Alkoholen in ungesättigte Kohlenwasserstoffe unter Einwirkung der Oxalsäure” Chem. Ber. 34, 3249 (1901)
What is Perkin rearrangement? The Perkin rearrangement is a chemical reaction that involves the contraction of the coumarin benzofuran ring. This reaction can be exemplified by the formation of both benzofuran-2-carboxylic acids and benzofurans, which occurs through the heating of 3-halocoumarins with an alkali. References W.H. Perkin, “XXIX.—On some new bromine derivatives of coumarin” J. … Read more
What is Overman rearrangement? The Overman rearrangement is a formal [3,3]-sigmatropic rearrangement of the trichloroacetimidate of allylic alcohols to allylic trichloroacetamides. Thus, transposing the hydroxyl and amino functions with chirality transfer. References Overman, L. E. “Thermal and mercuric ion catalyzed [3,3]-sigmatropic rearrangement of allylic trichloroacetimidates. 1,3 Transposition of alcohol and amine functions” J. Am. Chem. Soc.1974, … Read more
What is Tafel rearrangement? The Tafel rearrangement refers to a chemical reaction that involves the electrolytic reduction of substituted acetoacetic esters using a lead cathode in alcoholic sulfuric acid (H2SO4). During the reaction, the carbon skeleton of the ester undergoes a transformation, resulting in the production of hydrocarbons that have the same number of carbon … Read more
What is Stieglitz rearrangement? The Stieglitz rearrangement is a chemical reaction that involves the conversion of trityl hydroxylamines into Schiff bases upon treatment with phosphorus pentachloride. References Stieglitz, J. and Leech, P.N. (1913), Die molekulare Umlagerung von Triphenylmethyl-hydroxylamin. [The molecular rearrangement of triphenylmethyl-hydroxylamine.] Ber. Dtsch. Chem. Ges., 46: 2147-2151. https://doi.org/10.1002/cber.191304602134 The Molecular Rearrangement of Triarylmethyl-Hydroxylamines … Read more
What is Stevens rearrangement? The Stevens rearrangement is a chemical process that involves the migration of an alkyl group from a sulfonium or quaternary ammonium salt to an adjacent carbanionic center upon treatment with a strong base. This reaction ultimately leads to the formation of a rearranged tertiary amine or sulfide compound as the end … Read more
What is Wallach rearrangement? The Wallach rearrangement is a chemical reaction in which azoxybenzenes are rearranged under acidic conditions to produce p-hydroxyazobenzenes. This reaction is catalyzed by an acid and involves a rearrangement of the molecular structure. As a result of the Wallach rearrangement, the starting material, azoxybenzenes, are transformed into p-hydroxyazobenzenes. References Wallach, O. … Read more
What is Truce-Smiles rearrangement? The Truce-Smiles rearrangement, also referred to as the Smiles rearrangement, is a chemical reaction that involves an intramolecular nucleophilic aromatic substitution. This process occurs in an alkaline solution and leads to the movement of an aromatic system from one heteroatom to another within the same molecule. The connection between X and … Read more
What is Tiffeneau-Demjanov rearrangement? The Tiffeneau-Demjanov rearrangement refers to a chemical reaction that involves the expansion of the ring structure of β-amino alcohols upon diazotization with nitrous acid, resulting in the formation of carbonyl compounds. In addition to this, cyclic alcohols can also yield ring expanded or contracted products through this reaction. References M. Tiffeneau, … Read more
