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Darzens halogenation is the chemical synthesis of alkyl halides from alcohols via the treatment upon reflux of a large excess of thionyl chloride or thionyl bromide (SOX 2) in the presence of a small amount of a nitrogen base, such as a tertiary amine or pyridine or its corresponding hydrochloride or hydrobromide salt.
Some examples for this reaction were reported by Edward S. Lewis and Charles E. Boozer in 1952. [2] Mechanistic and kinetic studies were reported few years later by various researchers. [3] [4] Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite, actually forming an intimate ion pair.
Thionyl chloride is an inorganic compound with the chemical formula SOCl 2.It is a moderately volatile, colourless liquid with an unpleasant acrid odour.Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes (50,000 short tons) per year being produced during the early 1990s, [5] but is occasionally also used as a solvent.
The alcoholysis of acyl halides (the alkoxy-dehalogenation) is believed to proceed via an S N 2 mechanism (Scheme 10). [20] However, the mechanism can also be tetrahedral or S N 1 in highly polar solvents [21] (while the S N 2 reaction involves a concerted reaction, the tetrahedral addition-elimination pathway involves a discernible ...
The von Braun amide degradation is the chemical reaction of a monosubstituted amide with phosphorus pentachloride or thionyl chloride to give a nitrile and an organohalide. [1] It is named after Julius Jacob von Braun, who first reported the reaction. [2] [3] The von Braun amide degradation
Beckmann reaction. The reaction mechanism for this reaction is based on a catalytic cycle with cyanuric chloride activating the hydroxyl group via a nucleophilic aromatic substitution. The reaction product is dislodged and replaced by new reactant via an intermediate Meisenheimer complex. Beckmann cyanuric acid cataly cycle
The Hurd–Mori 1,2,3-thiadiazole synthesis is a name reaction in organic chemistry that allows for the generation of 1,2,3-thiadiazoles through the reaction of hydrazone derivatives with an N-acyl or N-tosyl group reacted with thionyl chloride.
The reaction is named after the German chemist, Emil Fischer, winner of the Nobel Prize in chemistry, 1902, who developed this method between 1893 and 1895. [1] [2] [3] Commonly, the reaction is performed using a solution or suspension of the carbohydrate in the alcohol as the solvent. The carbohydrate is usually completely unprotected.