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Tetra-n-propylammonium perruthenate a catalytic oxidant used in conjunction with N-methylmorpholine N-oxide for oxidation of primary & secondary alcohols to aldehydes and ketones.
Huan Cheng; Christian B W Stark. A double donor-activated ruthenium(VII) catalyst: synthesis of enantiomerically pure THF-diols. Angewandte Chemie. International edition in English. 2010, 49 (9), 1587-1590.
Brooks E Maki; Karl A Scheidt. Single-flask synthesis of N-acylated indoles by catalytic dehydrogenative coupling with primary alcohols. Organic Letters. 2009, 11 (7), 1651-1654.
Selective, catalytic oxidant introduced by Ley. Normally used in combination with N-methylmorpholine-N-oxide as the stoichiometric reoxidant and 4A molecular sieves to remove water. Preferred solvents are dichloromethane and acetonitrile. Primary and secondary alcohols are oxidized to aldehydes and ketones in high yield: J. Chem. Soc., Chem. Commun., 1625 (1987). For an example of alcohol to aldehyde oxidation in the partial synthesis of the acyl tetronic acid ionophore tetronasin, see: Tetrahedron Lett., 35, 319 (1994). Also useful for a number of other oxidations such as lactols to lactones and sulfides to sulfones. For oxidation of secondary amines to imines, and of hydroxylamines to nitrones, see: Tetrahedron Lett., 35, 6567, 6571 (1994).
For a comprehensive review of this reagent, see: Synthesis, 639 (1994). For a review of ruthenium oxo-complexes as organic oxidants, see: Chem. Soc. Rev., 21, 179 (1992).
For a brief feature on uses in synthesis, see: Synlett, 824 (2007).
Hazard Statements: H272-H315-H319-H335
May intensify fire; oxidizer. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P221-P210v-P220-P305+P351+P338-P405-P501a
Take any precaution to avoid mixing with combustibles. Keep away from heat Keep/Store away from clothing/combustible materials. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.