What does one get when bromine reacts with dimethylsulfoxide?
I tell you this product (?) has got to be the nastiest smelling stuff I've ever personally encountered.
The only thing that I can figure is that the Br attacks/replaces a H on the methyl group possibly similar to a bromoacetone formation. I'm not
sure if there is any tautoterism involved with the sulfoxide group as in the keto/enol group.
Also there was a bit of HBr necissarily present during the in situ production of Br2 from NaBr and H2SO4. I don't know if this impacted the end
product either.
Any clues?BromicAcid - 1-1-2005 at 05:30
Quote:
Bromination of DMSO with elemental bromine leads to the formation of trimethylsulfonium bromide. Methanesulfonic acid, paraformaldehyde, dimethyl
disulfide, and hydrogen bromide are formed as byproducts.
CH3SOCH3 --(Br2)--> (CH3)3S+Br- [75%]
From 'Technical Bulletin Reaction Solvent Dimethyl Sulfoxide (DMSO)' Gaylord Chemical Corporation
