Pfitzner-Moffatt oxidation acidic catalysts

In fact, the interference of amines in Pfitzner-Moffatt oxidations very often results from the trivial fact that basic sites in a molecule can quench the acidic catalyst. In such cases, the oxidations must be carried out by adding an excess of one equivalent of acidic catalyst. 

Perhydrohistrionicotoxin, 75, 611 Perhydrophenanthrene-9-one, 535 Periodates, 454 Periodic acid, 124 Peropyrene, 499 Peroxy adds, 260 Peroxybenzimidio acid, 455-456 Peroxycyclohexanecarboylic acid, 260 Persulfoxides, 241 Peterson reaction, 631, 636 Pfitzner-Moffatt oxidation, 227-228, 467 Phase-transfer catalysts, 10, 136, 159, 174-175, 191, 219, 249, 271, 404-406, 452, 565, 566, 586, 640-641 Phenacyldimethylsuifonium bromide, 456 Phenacyiidinedimethylsulfurane, 456 Phenanthrene, 35, 533, 669-670 9,10-Phenanthrenequinones, 47 6-477 Phenazines, 513... 

This fluorine-containing, oxidation-resistant alcohol is best oxidized by the Pfitzner-Moffatt reaction, using dichloroacetic acid as catalyst. Observe the use of toluene, instead of carcinogenic benzene, as solvent. A Swern oxidation was not reproducible, and caused substantial epimerization of the isobutyl side chain. Collins oxidation was successful, but ... 

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