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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-H500
May intensify fire; oxidizer. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May form combustible dust concentrations in air
Precautionary Statements: P210-P220-P221-P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Take any precaution to avoid mixing with combustibles. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant