VilsmeierâHaack reaction | |
---|---|
Named after |
Anton Vilsmeier Albrecht Haack |
Reaction type | Substitution reaction |
Identifiers | |
Organic Chemistry Portal | vilsmeier-reaction |
RSC ontology ID | RXNO:0000055 |
The VilsmeierâHaack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted formamide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5):
The reaction is named after Anton Vilsmeier and Albrecht Haack . [1] [2] [3]
For example, benzanilide and dimethylaniline react with phosphorus oxychloride to produce an unsymmetrical diaryl ketone. [4] Similarly, anthracene is formylated at the 9-position. [5] The reaction of anthracene with N-methylformanilide, also using phosphorus oxychloride, gives 9-anthracenecarboxaldehyde:
The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion (2), also called the Vilsmeier reagent. The initial product is an iminium ion (4b), which is hydrolyzed to the corresponding ketone or aldehyde during workup. [6]
The Vilsmeier-Haack reaction is widely used in organic chemistry for the synthesis of various compounds and is particularly useful for introducing carbonyl groups into aromatic compounds.
VilsmeierâHaack reaction | |
---|---|
Named after |
Anton Vilsmeier Albrecht Haack |
Reaction type | Substitution reaction |
Identifiers | |
Organic Chemistry Portal | vilsmeier-reaction |
RSC ontology ID | RXNO:0000055 |
The VilsmeierâHaack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted formamide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5):
The reaction is named after Anton Vilsmeier and Albrecht Haack . [1] [2] [3]
For example, benzanilide and dimethylaniline react with phosphorus oxychloride to produce an unsymmetrical diaryl ketone. [4] Similarly, anthracene is formylated at the 9-position. [5] The reaction of anthracene with N-methylformanilide, also using phosphorus oxychloride, gives 9-anthracenecarboxaldehyde:
The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion (2), also called the Vilsmeier reagent. The initial product is an iminium ion (4b), which is hydrolyzed to the corresponding ketone or aldehyde during workup. [6]
The Vilsmeier-Haack reaction is widely used in organic chemistry for the synthesis of various compounds and is particularly useful for introducing carbonyl groups into aromatic compounds.