Ruthenium tetroxide is a highly aggressive oxidant, but TPAP, which is its one-electron reduced derivative, is a mild
oxidizing agent for the conversion of
primary alcohols to
aldehydes (the Ley oxidation).[2] Secondary alcohols are similarly oxidized to
ketones.[3] It can also be used to oxidize primary alcohols all the way to the
carboxylic acid with a higher catalyst loading, larger amount of the cooxidant, and addition of two equivalents of water. In this situation, the aldehyde reacts with water to form the
geminal diolhydrate, which is then oxidized again.[4]
^Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. (1997). "Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis. Enantioselective total synthesis of Sch 38516 (Fluvirucin B1)". J. Am. Chem. Soc.119 (43): 10302–10316.
doi:
10.1021/ja972191k.
^Griffith, William P.;
Ley, Steven V.; Whitcombe, Gwynne P.; White, Andrew D. (1987). "Preparation and use of tetra-n-butylammonium per-ruthenate (TBAP reagent) and tetra-n-propylammonium per-ruthenate (TPAP reagent) as new catalytic oxidants for alcohols". J. Chem. Soc., Chem. Commun. (21): 1625–1627.
doi:
10.1039/C39870001625.