Sciencemadness Discussion Board

S2Cl2 by chlorination with CuCl2 in MeCN?

clearly_not_atara - 2-2-2024 at 09:29

Because of the formation of the acetonitrile-Cu+ complex, copper (II) is more strongly oxidizing in acetonitrile than in other common solvents. One source puts it at +0.56 V versus the standard carbon electrode, which is comparable to bromine.

https://books.google.com/books?hl=en&lr=&id=rYAkAQAA...

There are a few examples of chlorination of relatively resistant substrates with the CuCl2-acetonitrile system, such as coumarins:

https://pubs.rsc.org/en/content/articlelanding/2022/ob/d2ob0... (yes I know this is photocatalysis)

S2Cl2 is also apparently compatible with acetonitrile:

https://www.sciencedirect.com/science/article/pii/S004040390...

So it's interesting to me whether CuCl2 in acetonitrile would be reactive enough to chlorinate sulfur, possibly with some help from light. Half-cell potential is not a guarantee of reactivity, though.