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Phosphorus ylides are important reagents in organic chemistry, especially in the synthesis of naturally occurring products with biological and pharmacological activities. Much of the interest in the coordination properties of a-keto stabilized phosphorus ylides stems from their coordination versatility due to the presence of different ...
As pyridine is often used as an organic base in chemical reactions, pyridinium salts are produced in many acid-base reactions. 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.
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.
However, a few examples exist of a stepwise mechanism for the catalyst-free 1,3-dipolar cycloaddition reactions of thiocarbonyl ylides, [6] and nitrile oxides [7] The generic mechanism of a 1,3-dipolar cycloaddition between a dipole and a dipolarophile to give a five-membered heterocycle, through a six-electron transition state.
The Kröhnke pyridine synthesis is reaction in organic synthesis between α-pyridinium methyl ketone salts and α, β-unsaturated carbonyl compounds used to generate highly functionalized pyridines. Pyridines occur widely in natural and synthetic products, so there is wide interest in routes for their synthesis.
In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. [1] [2] With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spontaneously dimerize. Most organic radicals have short lifetimes.
The mechanism of oxidation under weakly basic (pyridine) conditions is similar, except that pyridine neutralizes the hydroxyammonium species, and this intermediate "comproportionates" with oxoammonium salt to give nitroxide radicals and pyridinium salts (see equation (3) below).
In a letter to Angewandte Chemie, the German chemist Manfred Christl [14] pointed out not only that the alleged new chemistry was in fact 100-year-old Zincke chemistry but also that the proposed structure for the reaction product was not the 12 membered ring but the 6 membered pyridinium salt (structure 2).