Sciencemadness Discussion Board

Stilbene Reactions

DraconicAcid - 1-11-2022 at 11:01

I have some stilbene (trans- the cheap stuff), and I'd like to do some chemistry with it. Bromination with HBr/H2O2 is apparently a simple experiment.
( https://web.centre.edu/workmanj/CHE%20241/STILBENE.htm#:~:te... )

Typical aromatic reactions such as FC alkylations and nitrations seem to be out of the question (from what I've read) because the double bond is more reactive than the ring.

Is there a clean way to oxidize it to benzil or benzoin? I've found a paper about its oxidation with chlorine dioxide to give a mess of products (some chlorinated), and its oxidation to the peroxide using organic peroxides that I'm reluctant to play with.

Texium - 1-11-2022 at 12:31

Oxidation to benzil with iodine and air in water: https://pubs.rsc.org/en/content/articlelanding/2013/RA/c3ra4...

DraconicAcid - 1-11-2022 at 13:49

Quote: Originally posted by Texium  
Oxidation to benzil with iodine and air in water: https://pubs.rsc.org/en/content/articlelanding/2013/RA/c3ra4...


W00T! Thank you!