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An ylide (/ ˈ ɪ l aɪ d /) [1] or ylid (/ ˈ ɪ l ɪ d /) is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons.
Pyridinium refers to the cation [C 5 H 5 NH] +. It is the conjugate acid of pyridine . Many related cations are known involving substituted pyridines, e.g. picolines, lutidines, collidines.
Radical disproportionation encompasses a group of reactions in organic chemistry in which two radicals react to form two different non-radical products. Radicals in chemistry are defined as reactive atoms or molecules that contain an unpaired electron or electrons in an open shell. The unpaired electrons can cause radicals to be unstable and ...
Radical dimerization of pyridine with elemental sodium or Raney nickel selectively yields 4,4'-bipyridine, [98] or 2,2'-bipyridine, [99] which are important precursor reagents in the chemical industry. One of the name reactions involving free radicals is the Minisci 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.
Radicals can propagate (k p) but also terminate (k t). However, persistent radicals (X), as stated above, cannot terminate with each other but only (reversibly) cross-couple with the growing species (k deact). Thus, every act of radical–radical termination is accompanied by the irreversible accumulation of X. Consequently, the concentration ...
The oxyl radicals are unstable and believed to be transformed into relatively stable carbon-centered radicals. For example, di-tert-butyl peroxide (t-Bu OOt-Bu) gives two t-butoxy radicals (t-BuO•) and the radicals become methyl radicals (CH 3 •) with the loss of acetone.
The Parikh–Doering oxidation is an oxidation reaction that transforms primary and secondary alcohols into aldehydes and ketones, respectively. [1] The procedure uses dimethyl sulfoxide (DMSO) as the oxidant and the solvent, activated by the sulfur trioxide pyridine complex (SO 3 •C 5 H 5 N) in the presence of triethylamine or diisopropylethylamine as base.