Tetrapropylammonium perruthenate,

A, A, A, A -tetramethylethylenediamine trimethyl orthoformate tetrapropylammonium perruthenate tetraphenylporphyrin sulfonated triphenylphosphine triisopropylbenzensulfonyl chloride triphenylcarbenium tetrafluoroborate tetrabutylammonium triphenylmethanethiolate toluenesulfonyl... 

In order to optimize oxidation conditions of diethyl(2-methylpyrrolidine-2-yl) phosphonate into the corresponding nitrone, a comparative analysis of the action of various oxidants such as H2O2, m-CPBA, Oxone, 2-phenylsulfonyl-3-phenyl-oxaziridine (PSPO), DMD, and A-methylrnorpholine /V-oxide in the presence of a catalytic quantity of tetrapropylammonium perruthenate (NMO/TPAP) has been made (92). 

Hydroboration occurred from the less hindered top face of rac-29 and resulted in the formation of alcohol rac-30. After a three-step sequence which included oxidation with tetrapropylammonium perruthenate (TPAP), methyl lithium addition and repeated oxidation with TPAP, ketone rac-31 was isolated. Finally, epimerization of the stereogenic center at C-7 to the correct configuration and methylenation with the Lombardo reagent led to the formation of racemic kelsoene (rac-1). 

Reductive alkylation of -caprolactone (1 equiv) with a 2 0.25 mixture of Grignard reagent and Zn(BH4)2 affords monoalkylated diols, which can be further selectively oxidized with tetrapropylammonium perruthenate (TPAP) into the expected monoalkylated lactones <2002CR571>. 

Most compounds of this type are derived from methyl hexosides methyl 2,6 3,4-dianhydro-a-D-altropyranoside309 398 400 516 and methyl 2,5 3,6-dianhydro-a- and /J-n-mannol iiranosides.517 From hexuloses, the synthetically useful l,5 3,6-dianhydro-D-<2raZ)i o-hex-2-ulose (172) has been prepared by regioselective monobenzylation of l,5 3,6-dianhydro-D-mannitol at C-4 (171a — 171b) followed by oxidation with tetrapropylammonium perruthenate.518... 

TPAP = Tetrapropylammonium perruthenate DMAP = 4-dimethylaminopyridine. NHO = N-methyl morpholine N-oxide ... 

S. V Ley, J. Norman, W. P. Griffith, S. P. Maraden, Tetrapropylammonium Perruthenate, Pr4N+Ru04, TPAP A Catalytic Oxidant for Organic Synthesis, Synthesis 1994, 639-666. 

The second example involves straightforward doping of methyl modified silica, denoted as ormosil, with tetrapropylammonium perruthenate via the sol-gel process [102] (Table 3). A serious disadvantage of this system are the low TOFs of 1.0 and 1.8 h 1 observed for a primary aliphatic alcohol and allylic alcohol, respectively. 

Fig. 14.14. TPAP oxidation of an alcohol to an aldehyde TPAP stands for tetrapropylammonium perruthenate.

Tetrapropylammonium perruthenate (0.027 mmol) was added to a mixture of (15,4/ )-4-(f-butyldimethylsilanyloxy)cyclopent-2-enol (0.54 mmol), 4-methylmorpholine IV-oxide (0.81 mmol), and 270 mg crushed 4 A molecular sieves dissolved in 10 ml CH2C12. The mixture was stirred 30 minutes at ambient temperature, then filtered through a plug of silica gel with CH2C12, concentrated, and the product isolated in 86% yield. 

---