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Its salts are often insoluble in the organic solvent, so precipitation of the pyridinium leaving group complex is an indication of the progress of the reaction. Pyridinium cations are aromatic, as determined through Hückel's rule. [4] They are isoelectronic with benzene.
In organic synthesis, PPTS is used as a weakly acidic catalyst, providing an organic soluble source of pyridinium (C 5 H 5 NH +) ions.For example, PPTS is used to deprotect silyl ethers or tetrahydropyranyl ethers when a substrate is unstable to stronger acid catalysts.
The second family of reagents are salts, featuring the pyridinium cation (C 5 H 5 NH +). pyridinium dichromate (PDC) is the pyridium salt of dichromate, [Cr 2 O 7] 2-. pyridinium chlorochromate (PCC) is the pyridinium salt of [CrO 3 Cl] −. These salts are less reactive, more easily handled, and more selective than Collins reagent in ...
The formation of the DNP-pyridinium salt. Upon heating a primary amine with the N-2,4-dinitrophenyl-pyridinium salt (2), the addition of the amine leads to the opening of the pyridinium ring. A second addition of amine leads to the displacement of 2,4-dinitroaniline (5) and formation of the König salt [5] (6a and 6b).
The reaction of pyridine with bromomethyl ketones gives the related pyridinium salt, wherein the methylene group is highly acidic. This species undergoes a Michael-like addition to α,β-unsaturated carbonyls in the presence of ammonium acetate to undergo ring closure and formation of the targeted substituted pyridine as well as pyridinium ...
Zincke aldehydes, or 5-aminopenta-2,4-dienals, are the product of the reaction of a pyridinium salt with two equivalents of any secondary amine, followed by basic hydrolysis. Using secondary amines (as opposed to primary amines) the Zincke reaction takes on a different shape forming Zincke aldehydes in which the pyridine ring is ring-opened ...
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In its chemical structure and functions, the Cornforth reagent is closely related to other pyridinium salts of hexavalent chromium oxide, such as pyridinium chlorochromate [PyH][CrO 3 Cl] and to pyridine complexes such as the Collins reagent, CrO 3 ·2Py in dichloromethane and the Sarret reagent, CrO 3 ·2Py in pyridine. [4]