Everything about Diphenyl Disulfide totally explained
| Section2 =
| Section3 =
| Section7 =
| Section8 =
}}
Diphenyl disulfide is the
chemical compound with the formula [C
6H
5S]
2. This colorless crystalline material is often abbreviated Ph
2S
2. It is one of the most popular organic
disulfides used in
organic synthesis. Minor contamination by
thiophenol is responsible for the disagreeable odour associated with this compound.
Preparation and structure
Ph
2S
2 is usually prepared by the oxidation of thiophenol:
» 2 PhSH +
I2 → Ph
2S
2 + 2 HI
Hydrogen peroxide can also be used as the oxidant. Ph
2S
2 is rarely prepared in the laboratory because it's inexpensive, and the precursor has a disagreeable odour.
Like most organic disulfides, the C
2S
2 core of Ph
2S
2 is non-planar with a dihedral angle approaching 85°.
Reactions
Ph
2S
2 is mainly used in organic synthesis as a source of the PhS substituent. A typical reaction entails the formation of PhS-substituted carbonyl compounds via the
enolate:
» RC(O)CHLiR’ + Ph
2S
2 → RC(O)CH(SPh)R’ + LiSPh
Reduction
Ph
2S
2 undergoes reduction, a reaction characteristic of disulfides:
» Ph
2S
2 + 2 M → 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 halides, RX (X = halide) convert it to the
thioethers with the general formula RSPh. Analogously, protonation of MSPh gives thiophenol:
» PhSM + HCl → HSPh + MCl
Chlorination
Ph
2S
2 reacts with
chlorine to give
phenylsulfenyl chloride PhSCl (
Zincke disulfide cleavage). This species is difficult to isolate, so it's usually generated in situ.
Catalyst for photoisomerisation of alkenes
Ph
2S
2catalyzes the cis-trans isomerization of alkenes under UV-irradiation.
Oxidation
Oxidation of Ph
2S
2 with
lead(IV) acetate (Pb(OAc)
4) in
methanol affords the sulfinite ester PhS(O)OMe.
Further Information
Get more info on 'Diphenyl Disulfide'.
|
External Link Exchanges
Do you know how hard it is to get a link from a large encyclopaedia? Well we're different and will prove it. To get a link from us just add the following HTML to your site on a relevant page:
<a href="http://diphenyl_disulfide.totallyexplained.com">Diphenyl disulfide Totally Explained</a>
Then simply click through this link from your web page. Our crawlers will verify your link, extract the title of your web page and instantly add a link back to it. If you like you can remove the words Totally Explained and embed the link in article text.
As long as your link remains in place, we'll keep our link to you right here. Please play fair - our crawlers are watching. Your site must be closely related to this one's topic. Any kind of spamming, dubious practises or removing the link will result in your link from us being dropped and, potentially, your whole site being banned. |
