DMSO Wacker

[Vibrating_Lights]

Has anyone ever tried to replace DMF with DMSO in an O2 Wacker?  DMSO is much more readily available.  ONe of DMSO's grewatest quailities it that it is a wonderful shuttler of Oxygen.  I see no reason why this would not work.

ALso when making an oxime with MDP2P and Hydroxylamine can MeOH be used in place of the EtOH.

[Rhodium]

Yes, MeOH can replace EtOH in most instances where the role of the alcohol just is as solvent, with possible adjustment in volume if the solubilities is different.

The only instances I can think of where the substitution does not work is in some sodium/ethanol reductions, some NaOEt/EtOH alkylations/condensations (as NaOMe is not as basic as NaOEt) and in some NaBH₄ reductions where MeOH decomposes the borohydride too fast. And naturally, you cannot make a substitution in those instances where ethanol is a reactant, for example if you want to make an ethyl ester by refluxing an acid in ethanol.

[Vibrating_Lights]

I found the info i needed for the DMSO wacker.  Why has no one here tried this shit yet.  O2 is alot fucking cheaper than Benzoquinone.  You know what else i been thinkin.  Why even go through the ketone.  WHat is stopping us from taking the palladium and forming the Complex then instead of using H2O Use MeNH3.  If what the palladium is doing is just drawing the H2O why the fuck wouldnt it draw the Amine?? IN fact a few weeks ago i found a ref about using an exotic palladium salt in a hydroamination rxn.  To the best of what i remember an exotic palladium was needed to provide enough attraction energy to make it happen but it did happen and in good yeilds.  I will see if i can find it again. I was tweeked at the time and i can't remember what i did with it for the life of me.  I do remember that it was very recently that this was developed.
VL_