Tetrapropylammonium perruthenate
| Tetrapropylammonium perruthenate | ||
|---|---|---|
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| IUPAC name Tetrapropylammonium perruthenate | ||
| Identifiers | ||
| Abbreviations | TPAP TPAPR | |
| CAS number | 114615-82-6  | |
| Jmol-3D images | {{#if:CCC[N+](CCC)(CCC)CCC.O=[Ru](=O)([O-])=O|Image 1 | |
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| Properties | ||
| Molecular formula | C12H28NRuO4 | |
| Molar mass | 351.43 g/mol | |
| Appearance | Green solid | |
| Melting point | 160 °C (decomposition) | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Tetrapropylammonium perruthenate (TPAP or TPAPR) is the chemical compound described by the formula N(C3H7)4RuO4. 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, RuO4− 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.[2] This oxidizing agent can also be used to oxidize primary alcohols all the way to the carboxylic acid. Use of a higher catalyst loading, larger amount of the co-oxidant, and addition of two equivalents of water. In this situation, the aldehyde reacts with water to form the geminal-diol hydrate, which is then oxidized again.[3]
The oxidation generates water that can be removed by adding molecular sieves. TPAP is expensive, but it can be used in catalytic amounts. The catalytic cycle is maintained by adding a stoichiometric amount of a co-oxidant such as N-methylmorpholine N-oxide or molecular oxygen.[4]
References
- ↑ A High-Yielding Synthesis of the Naturally Occurring Antitumour Agent Irisquinone John A. Hadfield, Alan T. McGown and John Butler Molecules 2000, 5, 82-88 Online Article
- ↑ Review: Steven V. Ley, Joanne Norman, William P. Griffith, Stephen P. Marsden, "Tetrapropylammonium Perruthenate, Pr4N+RuO4−, TPAP: A Catalytic Oxidant for Organic Synthesis" Synthesis, 1994, 639. doi:10.1055/s-1994-25538
- ↑ "Applications of Zr-Catalyzed Carbomagnesation and Mo-Catalyzed Macrocyclic Ring Closing Metathesis in Asymmetric Synthesis. Enantioselective Total Synthesis of Sch 38516 (Fluvirucin B1)" Z. Xu, C. W. Johannes, A. F. Houri, D. S. La, D. A. Cogan, G. E. Hofilena, A. H. Hoveyda, J. Am. Chem. Soc., 1997, 119, 10302
- ↑ "Tetra-n-propylammonium perruthenate (TPAP)-catalysed oxidations of alcohols using molecular oxygen as a co-oxidant" Roman Lenz and Steven V. Ley. J. Chem. Soc., Perkin Trans. 1, 1997, 3291. doi:10.1039/C39870001625
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