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Acyl halides are rather reactive compounds often synthesized to be used as intermediates in the synthesis of other organic compounds. For example, an acyl halide can react with: water, to form a carboxylic acid. This hydrolysis is the most heavily exploited reaction for acyl halides as it occurs in the industrial synthesis of acetic acid.
Acyl chlorides are used to prepare acid anhydrides, amides and esters, by reacting acid chlorides with: a salt of a carboxylic acid, an amine, or an alcohol, respectively. Acid halides are the most reactive acyl derivatives, and can easily be converted into any of the others. Acid halides will react with carboxylic acids to form anhydrides.
The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol . This reaction was developed by Alexander Williamson in 1850. [ 2 ] Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an S N 2 reaction .
Acyl halides and acid anhydrides of carboxylic acids are also common acylating agents. In some cases, active esters exhibit comparable reactivity. All react with amines to form amides and with alcohols to form esters by nucleophilic acyl substitution. Acylation can be used to prevent rearrangement reactions that would normally occur in alkylation.
Acetyl chloride is used for acetylation reactions, i.e., the introduction of an acetyl group. Acetyl is an acyl group having the formula −C(=O)−CH 3. For further information on the types of chemical reactions compounds such as acetyl chloride can undergo, see acyl halide.
Acyl azides have also been synthesized from various carboxylic acids and sodium azide in presence of triphenylphosphine and trichloroacetonitrile catalysts in excellent yields at mild conditions. [4] Another route starts with aliphatic and aromatic aldehydes reacting with iodine azide which is formed from sodium azide and iodine monochloride in ...
This reaction allows conservation of the carbonyl and halide functionalities. [28] The Büchner–Curtius–Schlotterbeck reaction used to insert a methylene bridge between a halogen and a cabonyl carbon of an acyl halide. It is possible to isolate nitrogen-containing compounds using the Büchner–Curtius–Schlotterbeck reaction.
In 1977, Migita published further work on the coupling of allyl-tin reagents with both aryl (C) and acyl (D) halides. The greater ability of allyl groups to migrate to the palladium catalyst allowed the reactions to be performed at lower temperatures. Yields for aryl halides ranged from 4% to 100%, and for acyl halides from 27% to 86%.