Diphenyl disulfide: Difference between revisions

| verifiedrevid = 402002389

| Name = Diphenyl disulfide

| ImageFile = Diphenyl disulfide.png

<!-- | ImageSize = 200px -->

| ImageName = Skeletal formula of diphenyl disulfide

| ImageFile1 = Diphenyl-disulfide-from-xtal-3D-balls.png

<!-- | ImageSize1 = 230px -->

| ImageName1 = Ball-and-stick model of diphenyl disulfide

| PIN = Disulfanyldibenzene

| IUPACName = Diphenyl disulfide

| OtherNames = Phenyl disulfide

| Section1 = {{Chembox Identifiers

| SMILES = c1ccc(cc1)SSc2ccccc2

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEMBL = 462861

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 882-33-7

| RTECS = SS6825000

| Section2 = {{Chembox Properties

| Formula = C₁₂H₁₀S₂

| MolarMass = 218.36 g/mol

| Appearance = Colourless crystals

| Density = ? g/cm³

| Solubility = Insoluble

| Solvent = other solvents

| SolubleOther = [[Diethyl ether]],<br />[[Benzene]],<br />[[Carbon disulfide]],<br />[[THF]]

| MeltingPt = 61–62 °C

| BoilingPt =

| Section3 = {{Chembox Structure

| CrystalStruct =

| Dipole = 0 [[Debye|D]]

| Section7 = {{Chembox Hazards

| ExternalMSDS =

| MainHazards = Flammable

| FlashPt =

| RPhrases = 36/37/38

| SPhrases = 26

| Section8 = {{Chembox Related

| OtherCpds = [[Thiophenol|C₆H₅SH]],<br />[[Dimethyl disulfide|(CH₃)₂S₂]],<br />[[Diphenyl diselenide]]

'''Diphenyl disulfide''' is the [[chemical compound]] with the formula [C₆H₅S]₂. This colorless crystalline material is often abbreviated Ph₂S₂. It is one of the most popular organic [[disulfide]]s used in [[organic synthesis]]. Minor contamination by [[thiophenol]] is responsible for the disagreeable odour associated with this compound.

Ph₂S₂ is usually prepared by the oxidation of thiophenol:

: 2 PhSH + [[iodine|I₂]] &rarr; Ph₂S₂ + 2 HI

[[Hydrogen peroxide]] can also be used as the oxidant.<ref>{{OrgSynth | author = Ravikumar,K. S.; Kesavan, V.; Crousse, B.; Bonnet-Delpon, D.; Bégué, J.-P. | title = Mild and Selective Oxidation of Sulfur Compounds in Trifluoroethanol: Diphenyl Disulfide and Methyl Phenyl Sulfoxide | volume = 80 | pages = 184 | year = 2003 | prep = v80p0184}}</ref> Ph₂S₂ is rarely prepared in the laboratory because it is inexpensive, and the precursor has a disagreeable odour.

Like most organic disulfides, the C₂S₂ core of Ph₂S₂ is non-planar with a dihedral angle approaching 85°.

Ph₂S₂ is mainly used in organic synthesis as a source of the PhS substituent.<ref>Byers, J. H. "Diphenyl Disulfide" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.</ref> A typical reaction entails the formation of PhS-substituted carbonyl compounds via the [[enolate]]:

:RC(O)CHLiR’ + Ph₂S₂ &rarr; RC(O)CH(SPh)R’ + LiSPh

:Ph₂S₂ + 2 M &rarr; 2 MSPh (M = Li, Na, K)

Hydride reagents such as [[sodium borohydride]] and [[super hydride]] can also be used as reductants.

The salts PhSM are sources of the potent [[nucleophile]] PhS^-. Most [[alkyl halide]]s, RX (X = halide) convert it to the [[thioether]]s with the general formula RSPh. Analogously, protonation of MSPh gives thiophenol:

:PhSM + HCl &rarr; HSPh + MCl

===Chlorination===

Ph₂S₂ reacts with [[chlorine]] to give [[phenylsulfenyl chloride]] PhSCl ([[Zincke disulfide cleavage]]). This species is somewhat difficult to isolate, so it is usually generated in situ.

===Catalyst for photoisomerisation of alkenes===

Ph₂S₂catalyzes the cis-trans isomerization of alkenes under UV-irradiation.<ref>{{OrgSynth | author = Thalmann, A. Oertle, K.; Gerlach, H. | title = Ricinelaidic Acid Lactone | collvol = 7 | collvolpages = 470 | year = 1990 | prep = cv7p0470}}</ref>

Oxidation of Ph₂S₂ with [[lead(IV) acetate]] (Pb(OAc)₄) in [[methanol]] affords the sulfinite ester PhS(O)OMe.<ref>{{OrgSynth | author = Field, L.; Locke, J. M. | title = Methyl Benzenesulfinate | collvol = 5 | collvolpages = 723 | year = 1973 | prep = cv5p0723}}</ref>

<references/>

[[Category:Aromatic compounds]]

[[ja:ジフェニルジスルフィド]]