Vilsmeier-Haack reaction
Overview
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...
of a substituted amide
Amide
In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...
(1) with phosphorus oxychloride and an electron-rich
Activating group
In organic chemistry, a functional group is called an activating group if a benzene molecule to which it is attached more readily participates in electrophilic substitution reactions...
arene
Arene
Arene or Arênê or Arène may refer to:*an aromatic hydrocarbon*Arene , a genus of marine snails in the family Areneidae*Arene , the wife of Aphareus and mother of Idas and Lynceus in Greek mythology...
(3) to produce an aryl
Aryl
In the context of organic molecules, aryl refers to any functional group or substituent derived from an aromatic ring, be it phenyl, naphthyl, thienyl, indolyl, etc....
aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
or ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
(5). The reaction is named after Anton Vilsmeier
Anton Vilsmeier
Anton Vilsmeier was a German chemist who together with Erich Haack discovered the Vilsmeier-Haack reaction.-Early life:...
and Albrecht Haack. The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion (2), also called the Vilsmeier reagent.
