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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
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.
Phosphorus trichloride is commonly used to convert primary and secondary alcohols to the corresponding chlorides. [14] As discussed above, the reaction of alcohols with phosphorus trichloride is sensitive to conditions. The mechanism for the ROH →RCl conversion involves the reaction of HCl with phosphite esters: P(OR) 3 + HCl ⇌ HP(OR) + 3 ...
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]
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 [11] is a well-suited reagent as the by-products (HCl, SO 2) are gases and residual thionyl chloride can be easily removed as a result of its low boiling point (76 °C). Phosphorus chlorides
People exposed to white phosphorus can suffer severe and sometimes deadly bone-deep burns. It can cause organs to shut down, and burns on just 10% of the body can be fatal, HRW said.
The usage of α-acyl sulfoxides and Lewis acids, such as TiCl 4 and SnCl 4, allow the reaction to proceed at lower temperatures (0 °C). [5] 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]