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Michael reaction

The Michael reaction or Michael addition is the nucleophilic addition of a carbanion or another nucleophile to an α,β-unsaturated carbonyl compound. It belongs to the larger class of conjugate additions. This is one of the most useful methods for ...

                                               

Michaelis–Arbuzov reaction

The Michaelis–Arbuzov reaction is the chemical reaction of a trivalent phosphorus ester with an alkyl halide to form a pentavalent phosphorus species and another alkyl halide. The picture below shows the most common types of substrates undergoing ...

                                               

Midland Alpine borane reduction

The Midland Alpine Borane Reduction, or simply the Midland Reduction, allows for the asymmetric reduction of carbonyls to alcohols. It was developed in the late 1970s by Professor M. Mark Midland at the University of California, Riverside. The Mi ...

                                               

Mislow–Evans rearrangement

The Mislow–Evans rearrangement is a name reaction in organic chemistry. It is named after Kurt Mislow and David A. Evans who discovered this reaction in 1971. The reaction allows the formation of allylic alcohols from allylic sulfoxides in a 2.3- ...

                                               

Mitsunobu reaction

The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate or diisopropyl azodicarboxylate. Altho ...

                                               

Mozingo reduction

The Mozingo reduction, also known as Mozingo reaction or thioketal reduction, is a chemical reaction capable of fully reducing a ketone or aldehyde to the corresponding alkane. The reaction scheme is as follows: The ketone or aldehyde is activate ...

                                               

Mukaiyama aldol addition

The Mukaiyama aldol addition is an organic reaction and a type of aldol reaction between a silyl enol ether and an aldehyde or formate. The reaction was discovered by Teruaki Mukaiyama in 1973. His choice of reactants allows for a crossed aldol r ...

                                               

Mumm rearrangement

The Mumm rearrangement is an organic reaction and a rearrangement reaction. It describes a 1.3 acyl transfer of an acyl imidate or isoimide group to an imide. The reaction is of relevance as part of the Ugi reaction.

                                               

Myers allene synthesis

In organic chemistry, the Myers allene synthesis is a chemical reaction that converts a propargyl alcohol into an allene by way of an arenesulfonylhydrazine as a key intermediate. This name reaction is one of two discovered by Andrew Myers that a ...

                                               

Myers deoxygenation

In organic chemistry, the Myers deoxygenation reaction is an organic redox reaction that reduces an alcohol into an alkyl position by way of an arenesulfonylhydrazine as a key intermediate. This name reaction is one of two discovered by Andrew My ...

                                               

Narasaka–Prasad reduction

The Narasaka–Prasad reduction, sometimes simply called Narasaka reduction, is a diastereoselective reduction of β-hydroxy ketones to the corresponding syn -dialcohols. The reaction employs a boron chelating agent, such as BBu 2 OMe, and a reducin ...

                                               

Nazarov cyclization reaction

The Nazarov cyclization reaction is a chemical reaction used in organic chemistry for the synthesis of cyclopentenones. The reaction is typically divided into classical and modern variants, depending on the reagents and substrates employed. It wa ...

                                               

Neber rearrangement

The Neber rearrangement is an organic reaction in which a ketoxime is converted into an alpha-aminoketone via a rearrangement reaction. The oxime is first converted to an O-sulfonate, for example a tosylate by reaction with tosyl chloride. Added ...

                                               

Nef isocyanide reaction

The Nef isocyanide reaction is an addition reaction that takes place between isocyanides and acyl chlorides to form imidoyl chloride products, a process first discovered by John Ulrich Nef. The reaction should not be confused with the better know ...

                                               

Nef reaction

The Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane to an aldehyde or a ketone and nitrous oxide. The reaction has been the subject of several literature reviews. The reaction was ...

                                               

Negishi coupling

The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds in the process. A palladium species is generall ...

                                               

Newman–Kwart rearrangement

The Newman–Kwart rearrangement is a type of rearrangement reaction in which the aryl group of an O -aryl thiocarbamate, ArOCNMe 2, migrates from the oxygen atom to the sulfur atom, forming an S -aryl thiocarbamate, ArSCNMe 2. The reaction is name ...

                                               

Nicholas reaction

The Nicholas reaction is an organic reaction where a dicobalt octacarbonyl-stabilized propargylic cation is reacted with a nucleophile. Oxidative demetallation gives the desired alkylated alkyne. It is named after Kenneth M. Nicholas. Several rev ...

                                               

Niementowski quinazoline synthesis

The Niementowski quinazoline synthesis is the chemical reaction of anthranilic acids with amides to form 4-oxo-3.4-dihydroquinazolines.

                                               

Niementowski quinoline synthesis

In 1894, Niementowski reported that 2-phenyl-4-hydroxyquinoline was formed when anthranilic acid and acetophenone were heated to 120–130 °C. He later found that at higher heat, 200 °C, anthranilic acid and heptaldehyde formed minimal yields of 4- ...

                                               

Nierenstein reaction

The Nierenstein reaction is an organic reaction describing the conversion of an acid chloride into a haloketone with diazomethane. It is an insertion reaction in that the methylene group from the diazomethane is inserted into the carbon-chlorine ...

                                               

Norrish reaction

The Norrish reaction in organic chemistry describes the photochemical reactions taking place with ketones and aldehydes. This type of reaction is subdivided in Norrish type I reactions and Norrish type II reactions. The reaction is named after Ro ...

                                               

Nozaki–Hiyama–Kishi reaction

The Nozaki–Hiyama–Kishi reaction is a nickel/chromium coupling reaction forming an alcohol from the reaction of an aldehyde with an allyl or vinyl halide. In their original 1977 publication, Tamejiro Hiyama and Hitoshi Nozaki reported on a chromi ...

                                               

Oppenauer oxidation

Oppenauer oxidation, named after Rupert Viktor Oppenauer, is a gentle method for selectively oxidizing secondary alcohols to ketones. The reaction is the opposite of Meerwein–Ponndorf–Verley reduction. The alcohol is oxidized with aluminium isopr ...

                                               

Overman rearrangement

The Overman rearrangement is a chemical reaction that can be described as a Claisen rearrangement of allylic alcohols to give allylic trichloroacetamides through an imidate intermediate. The Overman rearrangement was discovered in 1974 by Larry O ...

                                               

Oxo-Diels–Alder reaction

An oxo-Diels–Alder reaction is an organic reaction and a variation of the Diels–Alder reaction in which a suitable diene reacts with an aldehyde to form a dihydropyran ring. This reaction is of some importance to synthetic organic chemistry. The ...

                                               

Oxy-Cope rearrangement

In organic chemistry, the oxy-Cope rearrangement is a chemical reaction. It involves reorganization of the skeleton of certain unsaturated alcohols. It is a variation of the Cope rearrangement in which 1.5-dien-3-ols are converted to unsaturated ...

                                               

Parikh–Doering oxidation

The Parikh–Doering oxidation is an oxidation reaction that transforms primary and secondary alcohols into aldehydes and ketones, respectively. The procedure uses dimethyl sulfoxide as the oxidant, activated by the sulfur trioxide pyridine complex ...

                                               

Passerini reaction

The Passerini reaction is a chemical reaction involving an isocyanide, an aldehyde, and a carboxylic acid to form a α-acyloxy amide. This organic reaction was discovered by Mario Passerini in 1921 in Florence, Italy. It is the first isocyanide ba ...

                                               

Pauson–Khand reaction

The Pauson–Khand reaction is a chemical reaction described as a cycloaddition between an alkyne, an alkene and carbon monoxide to form a α,β-cyclopentenone. The reaction was discovered by Ihsan Ullah Khand, who was working as a postdoctoral assoc ...

                                               

Pechmann condensation

The Pechmann condensation is a synthesis of coumarins, starting from a phenol and a carboxylic acid or ester containing a β-carbonyl group. The condensation is performed under acidic conditions. The mechanism involves an esterification/transester ...

                                               

Pellizzari reaction

The Pellizzari reaction was discovered in 1911 by Guido Pellizzari, and is the organic reaction of an amide and a hydrazide to form a 1.2.4-triazole. The product is similar to that of the Einhorn-Brunner reaction, but the mechanism itself is not ...

                                               

Perkin reaction

The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin that is used to make cinnamic acids. It gives an α,β-unsaturated aromatic acid by the aldol condensation of an aromatic aldehyde and an acid anhydride, i ...

                                               

Perkow reaction

The Perkow reaction is an organic reaction in which a trialkyl phosphite ester reacts with a haloketone to form a dialkyl vinyl phosphate and an alkyl halide. In the related Michaelis–Arbuzov reaction the same reactants are known to form a beta-k ...

                                               

Petasis reaction

The Petasis reaction reaction) is the multi-component reaction of an amine, a carbonyl, and a vinyl- or aryl-boronic acid to form substituted amines. Reported in 1993 by Nicos Petasis as a practical method towards the synthesis of a geometrically ...

                                               

Peterson olefination

The Peterson olefination is the chemical reaction of α-silyl carbanions with ketones to form a β-hydroxysilane which eliminates to form alkenes. Several reviews have been published.

                                               

Petrenko-Kritschenko piperidone synthesis

The Petrenko-Kritschenko reaction is a classic multicomponent-name reaction that is closely related to the Robinson–Schopf tropinone synthesis, but was published 12 years earlier.

                                               

Pfitzinger reaction

The Pfitzinger reaction is the chemical reaction of isatin with base and a carbonyl compound to yield substituted quinoline-4-carboxylic acids. Several reviews have been published.

                                               

Pfitzner–Moffatt oxidation

The Pfitzner–Moffatt oxidation, sometimes referred to as simply the Moffatt oxidation, is a chemical reaction for the oxidation of primary and secondary alcohols to aldehydes and ketones, respectively. The oxidant is a combination of dimethyl sul ...

                                               

Piancatelli rearrangement

In 1976, the Italian chemist, Giovanni Piancatelli and coworkers developed a new method to synthesize 4-hydroxycyclopentenone derivatives from 2-furylcarbinols through an acid-catalyzed rearrangement. This discovery occurred when Piancatelli was ...

                                               

Pictet–Spengler reaction

The Pictet–Spengler reaction is a chemical reaction in which a β-arylethylamine undergoes condensation with an aldehyde or ketone followed by ring closure. The reaction was first discovered in 1911 by Ame Pictet and Theodor Spengler. Traditionall ...

                                               

Pinner reaction

The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt ; this is sometimes referred to as a Pinner salt. The reaction is named after Adolf Pinner, who first described it in 1877. Pinner ...

                                               

Pinnick oxidation

The Pinnick oxidation is an organic reaction by which aldehydes can be oxidized into their corresponding carboxylic acids using sodium chlorite under mild acidic conditions. It was originally developed by Lindgren and Nilsson. The typical reactio ...

                                               

Pomeranz–Fritsch reaction

The Pomeranz–Fritsch reaction, also named Pomeranz–Fritsch cyclization, is a named reaction in organic chemistry. It is named after Paul Fritsch and Casar Pomeranz. In general it is a synthesis of isoquinoline.

                                               

Povarov reaction

The Povarov reaction is an organic reaction described as a formal cycloaddition between an aromatic imine and an alkene. The imine in this organic reaction is a condensation reaction product from an aniline type compound and a benzaldehyde type c ...

                                               

Prato reaction

The Prato reaction is a particular example of the well-known 1.3-dipolar cycloaddition of azomethine ylides to olefins. In fullerene chemistry this reaction refers to the functionalization of fullerenes and nanotubes. The amino acid sarcosine rea ...

                                               

Prevost reaction

The Prevost reaction is chemical reaction in which an alkene is converted by iodine and the silver salt of benzoic acid to a vicinal diol with anti stereochemistry. The reaction was discovered by the French chemist Charles Prevost.

                                               

Prilezhaev reaction

The Prilezhaev reaction, also known as the Prileschajew reaction or Prilezhaev epoxidation, is the chemical reaction of an alkene with a peroxy acid to form epoxides. It is named after Nikolai Prilezhaev, who first reported this reaction in 1909. ...

                                               

Prins reaction

The Prins reaction is an organic reaction consisting of an electrophilic addition of an aldehyde or ketone to an alkene or alkyne followed by capture of a nucleophile or elimination of an H + ion. The outcome of the reaction depends on reaction c ...

                                               

Pschorr cyclization

The Pschorr cyclization is a name reaction in organic chemistry, which was named after its discoverer, the German chemist Robert Pschorr. It describes the intramolecular substitution of aromatic compounds via aryldiazonium salts as intermediates ...