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pinner reaction conditions

The nitrile ligands in the platinum(iv) complexes trans-[PtCl4(RCN)2] (R = Me, Et, CH2Ph) and cis/trans-[PtCl4(MeCN)(Me2 [[S with combining low line]] O)] are involved in a metalla-Pinner reaction with N-methylbenzohydroxamic acid (N-alkylated form of hydroxamic acid, …

Organic Chemistry Portal: Pinner Reaction. It will enhance any encyclopedic page you visit with the magic of the WIKI 2 technology.

Preparation and Utility of Trihaloethyl Imidates: Useful Reagents for the Mechanism of the Pinner Reaction To a solution of the SM (0.2 g, 0.3 mmol) in EtOH (5 mL) was added conc. Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. It has emphasized that this reaction must be carried out under anhydrous conditions. For example: an electron-poor nitrile is a good electrophile (readily susceptible to attack from alkoxides etc.) Pinner salts are themselves reactive and undergo additional nucleophilic additions to give various useful products: An efficient method for the conversion of aromatic and aliphatic nitriles to the corresponding N-tert-butyl amides: a modified Ritter reaction K. L. Reddy, Tetrahedron Lett., 2003, 44, 1453-1455. Die Hauptanwendung der Pinner-Reaktion ist die Herstellung von Carbonsäuren, Estern, Thioestern und Amiden. The Pinner reaction can be used to convert nitriles to esters. Dieses Salz kann dann weiter verarbeitet werden durch Umsetzung mit weiteren Reagenzien. Bei dieser Reaktion wird zunächst allgemein ein Pinner-Salz (4) hergestellt. [7] The determining factor is typically how electron-rich or poor the nitrile is. Die Elektronen der C-N-Dreifachbindung des Nitrils lagern sich um und es bildet sich die Iminogruppe 3 aus. Chem., 2010, 75, 945-947. The org phase was concentrated and the resulting residue was purified by silica gel chromatography (1:1 PE/EtOAc) to provide the product as a yellow solid. 75, 945-947. H 2 O-Catalyzed Ritter Reaction: A Convenient Synthesis of Amides from Esters and Nitriles C. Feng, B. Yan, G. Yin, J. Chen, M. Ji, Synlett, 2018, 29, 2257-2264. 2,2,2-Trifluoro- and trichloroethyl imidates, which are easily prepared by reaction of a nitrile and a trihaloethanol in the presence of HCl, are excellent reagents for the preparation of amidines under mild reaction conditions. Sie ist nach dem deutschen Chemiker Adolf Pinner (1842–1909) benannt. but a poor nucleophile would be difficult to protonate and hence would be expected to react more readily under basic rather than acidic conditions. Der Ausgangsstoff für alle Endprodukte der Pinner-Reaktion ist ein sogenanntes Pinner-Salz. According to the substitution and distribution patterns of groups on nitrogen, imidines can be divided into different categories. Chem., 2010, in one go. Berichte der deutschen chemischen Gesellschaft, "Ueber die Umwandlung der Nitrile in Imide", With hydrogen sulfide to form a thionoester. These The transformation of nitriles into imidines or their salts by the treatment of nitriles with an excess of strong acid and one equivalent of alcohol followed by an excess of ammonia or amines is generally known as the Pinner synthesis, or Pinner reaction. Browse other articles of this reference work: The full text of this article hosted at iucr.org is unavailable due to technical difficulties. The transformation of nitriles into imidines or their salts by the treatment of nitriles with an excess of strong acid and one equivalent of alcohol followed by an excess of ammonia or amines is generally known as the Pinner synthesis, or Pinner reaction. Des Weiteren lagert sich das Elektronenpaar zwischen dem Kohlenstoff- und dem Sauerstoffatom um. Learn more. Dadurch verlässt ein Alkoholat-Anion das Molekül. Name Reactions. Der Ausgangsstoff für alle Endprodukte der Pinner-Reaktion ist ein sogenanntes Pinner-Salz. HCl (5 mL). Ein Alkohol kann nun das Kohlenstoffatom der Nitrilgruppe nucleophil angreifen. It will enhance any encyclopedic page you visit with the magic of the WIKI 2 technology. [118 mg, 60%], [Patent Reference: WO2016011390, page 201, (20.2 MB)]. Die Aktivierung von Nitrilen erfolgt unter wasserfreien …

The most common alcohols employed are MeOH and EtOH, but many primary and secondary alcohols have been used. Lagert man keinen Alkohol an das Nitril, wie oben beschrieben, sondern ein Thiol oder ein Amin, so kann man auch Thioester bzw. Besides ethanol and methanol, … Dieses wird aus einem Nitril und einem Alkohol unter Einwirkung von Salzsäure hergestellt und liefert das Pinner-Salz, das Hydrochlorid eines Imidats. A less frequently used pyrolysis leads to carboxamides (Scheme€3) [3-5]. [1] Versetzt man das Pinner-Salz (4) mit Wasser, bildet sich ein Oxonium-Ion 5. The two approaches can be complementary, with nitriles which are unreactive under acid conditions often giving better results in the presence of base, and vice versa. Somit verlässt in der Summe ein Ammonium-Ion das Molekül. [4.0 g, 94%], [Patent Reference: WO2014149164, page 234, (23.7 MB)], A solution of the SM (180 mg, 0.53 mmol) in MeOH (50 mL) and H2SO4 (2 mL) was refluxed for 16 h. After concentration, the residue was dissolved in DCM (100 mL) and adjusted to pH = 8 with 3N NaOH. The high toxicity and the laborious handling of gaseous hydrogen chloride are further drawbacks of this reaction. Pinner reaction by bubbling anhydrous HCl gas into an equimolar mixture of aromatic or benzylic nitrile.

Dadurch entsteht ein Ammonium mit Hydroxygruppe 6.

Dadurch bildet sich Juni 2020 um 09:06 Uhr bearbeitet. ein Carbonsäureester 7. Durch Umlagerung eines Elektronenpaars bildet sich wieder eine Doppelbindung zwischen dem Stickstoff- und dem Kohlenstoff-Atom aus. and you may need to create a new Wiley Online Library account. Besides ethanol and methanol, other alcohols have also been found suitable for this reaction. Would you like Wikipedia to always look as professional and up-to-date? Related Reactions (Pinner Reaction) Examples: Example 1. Pinner Reaction. The reaction was kept standing for 16 h, after which time the reaction mixture was concentrated in vacuo.

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