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Pyridinium perbromide (also called pyridinium bromide perbromide, pyridine hydrobromide perbromide, or pyridinium tribromide) is an organic chemical composed of a pyridinium cation and a tribromide anion. It can also be considered as a complex containing pyridinium bromide—the salt of pyridine and hydrogen bromide—with an added bromine (Br ...
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.
Tribromide is the anion with the chemical formula Br 3 −, or salts containing it: . Tetrabutylammonium tribromide; Tetrabromophosphonium tribromide; Pyridinium perbromide; Sodium and potassium tribromides can be prepared by reacting NaBr or KBr with aqueous bromine.
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The pyridinium cation is isoelectronic with benzene. Pyridinium p - toluenesulfonate (PPTS) is an illustrative pyridinium salt; it is produced by treating pyridine with p -toluenesulfonic acid . In addition to protonation , pyridine undergoes N-centred alkylation , acylation , and N -oxidation .
The Cornforth reagent (pyridinium dichromate or PDC) is a pyridinium salt of dichromate with the chemical formula [C 5 H 5 NH] 2 [Cr 2 O 7].This compound is named after the Australian-British chemist Sir John Warcup Cornforth (b. 1917) who introduced it in 1962.
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.