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Chapter 16: Ethers, Epoxides
and Sulfides |
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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.
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dimethyl sulfide
methylthiomethane
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ethyl methyl sulfide
methylthioethane
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thiirane
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thiane
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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)
Reactivity:
- 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)
