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Pyridine is a basic heterocyclic organic compound with the chemical formula C 5 H 5 N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom (=N−). It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell.
One family of reagents employs the complex CrO 3 (pyridine) 2. [2] Sarett's reagent: a solution of CrO 3 (pyridine) 2 in pyridine. It was popularized for selective oxidation of primary and secondary alcohols to carbonyl compounds. Collins reagent is a solution of the same CrO 3 (pyridine) 2 but in dichloromethane. The Ratcliffe variant of ...
The broad scope of the Kröhnke pyridine synthesis has made it particularly useful for the synthesis of poly aryl systems including pyridyl, thienyl, and furanyl moieties as well. The method tolerates a broad array of aryl substitiuents on both the α-pyridinium methyl ketone fragment and the α, β-unsaturated carbonyl compounds and can thus ...
One possible way to do a substitution on pyridine is nucleophilic aromatic substitution. Even with no catalysts, the nitrogen atom, being electronegative, can hold the negative charge by itself. Another way is to do an oxidation before the electrophilic substitution. This makes pyridine N-oxide, which due to the negative oxygen atom, makes the ...
The role of pyridine as a Lewis base extends also to main group chemistry. Examples include sulfur trioxide pyridine complex SO 3 (py) and pyridine adduct of borane, BH 3 py. Pyridine is classified as L ligand in the Covalent bond classification method. In the usual electron counting method, it is a two-electron ligand.
Different aromatic nitrogen heterocyclic compounds proceed through the Chichibabin reaction in a matter of minutes and others can take hours. Factors that influence the reaction rate include: Basicity - The ideal pKa range is 5-8 and the reaction either does not proceed, or proceeds poorly outside of this range. The reaction occurs faster under ...
The original Knorr synthesis employed two equivalents of ethyl acetoacetate, one of which was converted to ethyl 2-oximinoacetoacetate by dissolving it in glacial acetic acid, and slowly adding one equivalent of saturated aqueous sodium nitrite, under external cooling. Zinc dust was then stirred in, reducing the oxime group to the amine. This ...
The synthesis of tropinone can be seen as a variation of the Petrenko-Kritschenko reaction in which the two aldehyde functions are covalently linked in a single molecule. Apart from the Hantzsch synthesis the Petrenko-Kritschenko reaction is one of the few examples in which a symmetric pyridine precursor can be obtained in a multicomponent ring ...