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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.
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]
It occurs in compounds such as thionyl fluoride, SOF 2. Thionyl chloride , SOCl 2 , is a common reagent used in organic synthesis to convert carboxylic acids to acyl chlorides . In organic chemistry , the thionyl group is known as a sulfoxide group or sulfinyl group, and has the general structure RS(=O)R'.
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
Acyl compounds react with nucleophiles via an addition mechanism: the nucleophile attacks the carbonyl carbon, forming a tetrahedral intermediate. This reaction can be accelerated by acidic conditions, which make the carbonyl more electrophilic, or basic conditions, which provide a more anionic and therefore more reactive nucleophile.
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]
Thionyl chloride can be used in place of acetic anhydride to trigger the elimination for forming the electrophilic intermediate and supplying chloride as the nucleophile to give an α-chloro-thioether: [6] Example of the Pummerer rearrangement using thionyl chloride. Other anhydrides and acyl halides can give similar products. Inorganic acids ...
Tertiary alcohols react with hydrochloric acid to produce tertiary alkyl chloride. Primary and secondary alcohols are converted to the corresponding chlorides using thionyl chloride and various phosphorus chloride reagents. [38] Primary and secondary alcohols, likewise, convert to alkyl bromides using phosphorus tribromide, for example: