Chapter 16: Ethers, Epoxides and Sulfides

Sulfides

Nomenclature:
Functional group suffix =  thioether or sulfide (review)
Functional group prefix = alkylthio-
Whereas "ox-" is used for oxygen containing systems, the sulfur analogues are "thi-".
Otherwise, the nomenclature is similar to that of ethers.
 

Structure:

• The sulfide functional group consists of a S atom bonded to two C atoms via s bonds.
• C-S bonds (approx. 181 pm) are longer than analogous C-O bonds (approx. 141 pm)

• Sulfides can be oxidised to sulfoxides or, if the oxidant is strong enough to sulfones.
• Sodium metaperiodate, NaIO₄ is suitable for sulfide to sulfoxide.
• Peracids can be used for both sulfide to sulfoxide and sulfoxide to sulfone (stoichiometry)