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Sulfone
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Sulfone
In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl (R−S(=O)2−R') functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms[dubious – discuss] and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents.
Sulfones are typically prepared by organic oxidation of thioethers, often referred to as sulfides. Sulfoxides are intermediates in this route. For example, dimethyl sulfide oxidizes to dimethyl sulfoxide and then to dimethyl sulfone.
Sulfur dioxide participates in cycloaddition reactions with dienes. For example, the industrially useful solvent sulfolane is prepared by addition of sulfur dioxide to buta-1,3-diene followed by hydrogenation of the resulting sulfolene.
Sulfones are prepared under conditions used for Friedel–Crafts reactions using sources of RSO+
2 derived from sulfonyl halides and sulfonic acid anhydrides. Lewis acid catalysts such as AlCl3 and FeCl3 are required.
Sulfones have been prepared through nucleophilic displacement of halides by sulfinates: In general, relatively nonpolar ("soft") alkylating agents react with sulfinic acids to give sulfones, whereas polarized ("hard") alkylating agents form esters. Allyl, propargyl, and benzyl sulfinates can thermally rearrange to the sulfone. Esters without an activated bond generally do not so rearrange.
![{\displaystyle {\mathrm {ArSO} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {Na} {}+{}\mathrm {Ar} {\vphantom {A}}^{\prime }\mathrm {Cl} {}\mathrel {\longrightarrow } {}\mathrm {Ar} (\mathrm {Ar} {\vphantom {A}}^{\prime })\mathrm {SO} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}\mathrm {NaCl} }}](https://wikimedia.org/api/rest_v1/media/math/render/svg/5417786f3ed60718a62edfc38cdd459157847cb0)
A relatively inert functional group, sulfones are typically less oxidizing and only 4 bel more acidic than sulfoxides. They eventually eliminate to an alkene in base, but leave about 9 bel more slowly than chloride. In the Ramberg–Bäcklund reaction and the Julia olefination, sulfones eliminate sulfur dioxide to form an alkene.
Sulfones are strongly electron-withdrawing, and vinyl sulfones are electrophilic Michael acceptors.
The behavior of the α carbon depends on context. Non-nucleophilic bases deprotonate to an enolate-like carbanion. Contrariwise, Lewis acids on the sulfone oxygens give a Pummerer-like electrophile that undergoes nucleophilic substitution.
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Sulfone
In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl (R−S(=O)2−R') functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms[dubious – discuss] and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents.
Sulfones are typically prepared by organic oxidation of thioethers, often referred to as sulfides. Sulfoxides are intermediates in this route. For example, dimethyl sulfide oxidizes to dimethyl sulfoxide and then to dimethyl sulfone.
Sulfur dioxide participates in cycloaddition reactions with dienes. For example, the industrially useful solvent sulfolane is prepared by addition of sulfur dioxide to buta-1,3-diene followed by hydrogenation of the resulting sulfolene.
Sulfones are prepared under conditions used for Friedel–Crafts reactions using sources of RSO+
2 derived from sulfonyl halides and sulfonic acid anhydrides. Lewis acid catalysts such as AlCl3 and FeCl3 are required.
Sulfones have been prepared through nucleophilic displacement of halides by sulfinates: In general, relatively nonpolar ("soft") alkylating agents react with sulfinic acids to give sulfones, whereas polarized ("hard") alkylating agents form esters. Allyl, propargyl, and benzyl sulfinates can thermally rearrange to the sulfone. Esters without an activated bond generally do not so rearrange.
A relatively inert functional group, sulfones are typically less oxidizing and only 4 bel more acidic than sulfoxides. They eventually eliminate to an alkene in base, but leave about 9 bel more slowly than chloride. In the Ramberg–Bäcklund reaction and the Julia olefination, sulfones eliminate sulfur dioxide to form an alkene.
Sulfones are strongly electron-withdrawing, and vinyl sulfones are electrophilic Michael acceptors.
The behavior of the α carbon depends on context. Non-nucleophilic bases deprotonate to an enolate-like carbanion. Contrariwise, Lewis acids on the sulfone oxygens give a Pummerer-like electrophile that undergoes nucleophilic substitution.
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