TPAP tetrapropyl

Tetra-n-propylammonium perruthenate (TPAP, tetrapropyl tetraoxoruthenate) [114615-82-6] M 351.4, m 160"(dec). It is a strong oxidant and may explode on heating. It can be washed with aq n-propanol, then H2O and dried over KOH in a vac. It is stable at room temp but best stored in a refrigerator. It is sol in CH2CI2 and MeCN. [Dengel et al. Transition Met Chem 10 98 1985 Griffith et al. J Chem Soc, Chem Commun 1625 1987.] Polymer supported reagent is available commercially. 

A C-nor derivative that retained the oxetane ring was formed by oxidation of 2 -protected diol with tetrapropyl-ammonium perruthenate (TPAP), which oxidized the C-6 hydroxyl group selectively to give an unstable 7-hydroxy-6-keto derivative. This derivative then underwent a retro-aldol reaction followed by an aldol reaction to give the C-nortaxol 4.2.2.4 unfortunately the deprotected final product 4.2.2.S was unstable and could not be completely characterized (779). 

Toluene, 75-85 °C 10mol% polymer- supported perruthenate (PSP) > Toluene, 70-80 °C, 4AmS, 5mol% tetrapropyl- ammoniumperruthenate (TPAP) > Toluene, 75 °C, 10mol% TPAP-doped sol-gel ormosil )... 

Substrate Toluene, 75-85°C 10 mol% polymer supported perruthenate (PSP) Carbonyl yield Toluene, 70-80 C, 4AMS,5mol% tetrapropyl-ammo- niumperruthenate TPAP) Toluene, 75 C, 10mol%TPAP doped sol-gel omtosil ... 

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