Sciencemadness Discussion Board

Reaction of sulfur chlorides with alcohols

Triflic Acid - 15-3-2021 at 18:46

I am trying to find some sort of literature that outlines the reaction of sulfur chlorides with alcohols. As much as I search, I can't find anything. I could only find two useless things on PubChem,
Quote:

Alcohol and glycols in the presence of hydrochloric acid lead to dehydration reactions.


and

Quote:

Decomp in alcohol, ether


I am trying to see if this reaction will form alkyl chlorides and an analogous reaction will form alkyl iodides (More details here). Before I start experimenting, I want some literature of sorts that confirms that this works. Does anyone have a paper outlining this?

Maurice-VD-3 - 20-3-2021 at 12:20

This problem was probably studied at the end of the 19th century.

clearly_not_atara - 20-3-2021 at 13:59

That's because the rxns give a mixture of products including, among other things, sulfur mustards. The dehydration product alkenes can add across S-Cl to give further products.