114615-82-6 Tetrapropylammonium Perruthenate (TPAP)

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UN1479 5.1/PG2

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).