reduction of dmso

[stratosphere]

i would figure dmso would require only weak reducing agent to be converted to dms, i was looking for a free-energy table to see if Sn(II) would reduce it under basic conditions (acidic condition must be avoided becuase the creation of methylthiol would be undesirable and stinky.
if you know where a extensive thermo/free-energy table is on the web please point me out.

but if this (or someother basic aqueous reduction) were to reduce dmso to dms, it would presumably hydrolyze to form MeSNa, and MeOH.

after isolating the MeSNa, reacting this with a weak oxidizing agent (perhaps excess sulpher), should give dimethyl polysulfide, which could be extracted into a non-polar solvent, and would presumably make a good methylating agent.

actually a way to reduce dmso to dms , without hydrolysis in the presence of excess sulpher would be more desirable, as it would allow you to directly create the dimethyl polysulfide. and would only require half the dmso to create the same amount of dimethyl polysulfide.

[hest]

Molecule:

DMSO ("CS(o)C ")

Molecule:

DMS (" COS(O)(O)OC ")


see the problem  

[hypo]

i guess stratosphere is talking about DiMethylSulfide,
proving again that ambiguous acronyms (AAs) are _evil_.

[stratosphere]

yeah, i meant dimethylsulfide by dms. sorry for the ambiguity.
really by reading all of my post hest, i think it should have been obvious what i meant, in fact at the end i said dimethylpolysufide several times.

[Antibody2]

Al/Hg will reduce DMSO. Ab2 thought DMSO might make a good solvent for another reduction he was working on and ended up reducing the solvent as well  lol.

[stratosphere]

was the addition of HCl necassary for the reduction to occur, or did the dmso react on contact with the Al/Hg?

[Antibody2]

HOAc was used with the Al/Hg as 10% of the solvent volume. There were no attempts without the HOAc as trials with other solvents demonstrated that an acid was necessary (to reduce the oxime).

There wasn't much effort put into this solvent system (only ran it twice) because of the horrible odour the reduced dmso made.

Rotten tomatoes was how someone who was visiting described the smell

[stratosphere]

if one wanted to persue this, the addition of excess S might aid in creating the dimethyl polysulfide, which would be less volatile and less stinky, although i don't know if H2S would also form under those conditions, being stinky + very toxic obviously that would be bad.

perhaps CH3I is easier to create and work with, despite its expense, the iodine could always be recycled.