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A typical representative organic reaction displaying this mechanism is the chlorination of alcohols with thionyl chloride, or the decomposition of alkyl chloroformates, the main feature is retention of stereochemical configuration. Some examples for this reaction were reported by Edward S. Lewis and Charles E. Boozer in 1952. [2]
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 S N i mechanism is observed in reactions of thionyl chloride with alcohols, and it is similar to S N 1 except that the nucleophile is delivered from the same side as the leaving group. Nucleophilic substitutions can be accompanied by an allylic rearrangement as seen in reactions such as the Ferrier rearrangement .
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.
The acid chloride then reacts with diazomethane (R 2 = H), or occasionally a diazoalkyl, via the Arndt-Eistert procedure, to generate an α-diazo ketone, which will undergo a metal-catalyzed or photolyzed Wolff rearrangement, to give a ketene. The ketene can be trapped with any weak acid, such as an alcohol or amine, to form the ester or amide.
The Beckmann rearrangement is often catalyzed by acid; however, other reagents have been known to promote the rearrangement. These include tosyl chloride, thionyl chloride, phosphorus pentachloride, phosphorus pentoxide, triethylamine, sodium hydroxide, trimethylsilyl iodide among others. [3]
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl , where R is a side chain . They are reactive derivatives of carboxylic acids ( R−C(=O)OH ).
It can be thought of chemically as the double acyl chloride analog of carbonic acid, or structurally as formaldehyde with the hydrogen atoms replaced by chlorine atoms. In 2013, about 75–80 % of global phosgene was consumed for isocyanates , 18% for polycarbonates and about 5% for other fine chemicals .