Tetrapropylammonium perruthenate

Tetrapropylammonium Perruthenate

Tetrapropylammonium perruthenate

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Tetrapropylammonium perruthenate (TPAP or TPAPR) is the chemical compound described by the formula N(C<sub>3</sub>H<sub>7</sub>)<sub>4</sub>RuO<sub>4</sub>. Sometimes known as the Ley-Griffith reagent, this ruthenium compound is used as a reagent in organic synthesis. This salt consists of the tetrapropylammonium cation and the perruthenate, RuO<sub>4</sub><sup><nowiki>&minus;</nowiki></sup> anion. Ruthenium tetroxide is a highly aggressive oxidant, but its one-electron reduced derivative is a mild oxidizing agent for the conversion of alcohols to aldehydes.Review: Steven V. Ley, Joanne Norman, William P. Griffith, Stephen P. Marsden, "Tetrapropylammonium Perruthenate, Pr<sub>4</sub>N<sup>+</sup>RuO<sub>4</sub><sup><nowiki>&minus;</nowiki></sup>, TPAP: A Catalytic Oxidant for Organic Synthesis" Synthesis, 1994, 639. This oxidizing agent can also be used to oxidize primary alcohols all the way to the carboxylic acid through a higher catalyst and co-oxidant loading along with the addition of two equivalents of water. The mechanism works by a normal oxidation of the alcohol to the aldehyde followed by hydration, and a final oxidation."Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective...
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