Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
The Vilsmeier reagent is an organic compound with the formula [(CH3)2NCHCl]Cl. It is a salt consisting of the N,N-dimethyliminium cation ([(CH3)2N=CHCl]+) and chloride anion. Depending on the particular reaction, the anion can vary. In typical POCl3-based reactions, the anion is PO2Cl2−. The iminium cation [(CH3)2N=CHCl]+ is the reactive component of interest. This iminium species is a derivative of the imidoyl chloride CH3N=CHCl. Analogues of this particular reagent are generated when tertiary amides other than DMF are treated with POCl3.
The salt is a white solid that is soluble in polar organic solvents. Vilsmeier reagent is the active intermediate in the formylation reactions, the Vilsmeier reaction or Vilsmeier-Haack reaction that use mixtures of dimethylformamide and phosphorus oxychloride to generate the Vilsmeier reagent, which in turn attacks a nucleophilic substrate and eventually hydrolyzes to give formyl. It is a source of "O=CH+".[1]
Pathway for formation of Vilsmeier reagent and its mode of action.[2]
^Paul R. Giles; Charles M. Marson (2001). "Dimethylchloromethyleneammonium Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd319m. ISBN 0-471-93623-5.
^Jones, G.; Stanforth, S. P. (2000). "The Vilsmeier Reaction of Non-Aromatic Compounds". Org. React.56 (2): 355–686. doi:10.1002/0471264180.or056.02.
The Vilsmeierreagent is an organic compound with the formula [(CH3)2NCHCl]Cl. It is a salt consisting of the N,N-dimethyliminium cation ([(CH3)2N=CHCl]+)...
[(CH3)2N=CH(Cl)]+, known as a Vilsmeierreagent, which attacks arenes. Organolithium compounds and Grignard reagents react with DMF to give aldehydes...
the pharmaceutical industry. In the Vilsmeier-Haack reaction, POCl3 reacts with amides to produce a "Vilsmeierreagent", a chloro-iminium salt, which subsequently...
called the Vilsmeierreagent, [(CH3)2N=CClH]Cl. More typically, a related salt is generated from the reaction of DMF and POCl3. Such reagents are useful...
DMF to form a Vilsmeierreagent, followed by a ring opening by chloride ions. Aryl chlorides can also be produced using a Vilsmeierreagent from triphosgene...
dimethylformamide (DMF), which reacts with oxalyl chloride to give the Vilsmeierreagent, an iminium intermediate that which reacts with the carboxylic acid...
Stephen aldehyde synthesis Stork enamine alkylation Vilsmeier-Haack reaction and Vilsmeierreagent Iminylium ions have the general structure R2C=N+. They...
A reagent that delivers the formyl group is called a formylating agent. Formic acid Dimethylformamide and phosphorus oxychloride in the Vilsmeier-Haack...
chloroiminium ions; as such a reaction with dimethylformamide will form the Vilsmeierreagent. By an analogous process primary amides will react with thionyl chloride...
sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis. Oxalyl chloride was first prepared in 1892 by the...
forms (if volatile) or milder reagents such as PCC are used. [O] + CH3(CH2)9OH → CH3(CH2)8CHO + H2O A variety of reagent systems achieve aldehydes under...
also available. Many specialized methods also yield amides. A variety of reagents, e.g. tris(2,2,2-trifluoroethyl) borate have been developed for specialized...
Dimethylcarbamoyl chloride (DMCC) is a reagent for transferring a dimethylcarbamoyl group to alcoholic or phenolic hydroxyl groups forming dimethyl carbamates...
Well-known reactions and reagents in organic chemistry include Contents: A B C D E F G H I J K L M N O P Q R S T U V W X Y Z See also External links 1...
phosphorylated serine in the biosynthesis of the amino acid tryptophan. Vilsmeier–Haack formylation of indole will take place at room temperature exclusively...
also consists of three steps, as shown in figure 3. First off, a Vilsmeier-Haack reagent is prepared by refluxing paraformaldehyde and dimethylamine hydrochloride...
pp. 91–129 (see pp. 99, 113). ISBN 978-0-231-05694-6. Ammer H, Besl H, Vilsmeier S (1997). "Der Flaschensporige Goldschimmel, Sepedonium ampullosporum –...
Global Information
