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Diphenyl disulfide is the chemical compound with the formula (C 6 H 5 S) 2. This colorless crystalline material is often abbreviated Ph 2 S 2. It is one of the more commonly encountered organic disulfides in organic synthesis. Minor contamination by thiophenol is responsible for the disagreeable odour associated with this compound.
The S-S bond length is 2.03 Å in diphenyl disulfide, [1] similar to that in elemental sulfur. Two kinds of disulfides are recognized, symmetric and unsymmetric. Symmetrical disulfides are compounds of the formula RSSR. Most disulfides encountered in organo sulfur chemistry are symmetrical disulfides.
Diphenyl sulfide and its analogues can also be produced by coupling reactions using metal catalysts. [5] It can also be prepared by reduction of diphenyl sulfone. [6] Diphenyl sulfide is a product of the photodegradation of the fungicide edifenphos. [7] Diphenyl sulfide is a precursor to triaryl sulfonium salts, which are used as photoinitiators.
General structure of a disulfide Organic disulfides are chemical compounds with the general structure RSSR'. Wikimedia Commons has media related to Organic disulfides .
Diphenyl disulfide reacts with alkynes to a 1,2-bis(phenylthio)ethylene. [21] Reported alkynes are ynamides. [ 22 ] A photoredox thiol-yne reaction has been reported.
Sulfur–sulfur bonds are a structural component used to stiffen rubber, similar to the disulfide bridges that rigidify proteins (see biological below). In the most common type of industrial "curing" or hardening and strengthening of natural rubber , elemental sulfur is heated with the rubber to the point that chemical reactions form disulfide ...
Methyl methanethiosulfinate can also disproportionate to a 1:1 mixture of dimethyl disulfide and methyl methanethiosulfonate (CH 3 SO 2 SCH 3) and rearrange via a Pummerer rearrangement to CH 3 S(O)CH 2 SSCH 3. [20] [21] An unusual three-membered ring thiosulfinate (a dithiirane 1-oxide) has been prepared through rearrangement of a 1,3 ...
Description: Skeletal formula of the diphenyl disulfide molecule.. Structure based on X-ray crystallographic data reported in J. Am. Chem. Soc. 132, 5799–5802. Image generated in ChemDraw Professional 19.0 and converted into SVG file using Scribus 1.5.4 + Inkscape 1.0.1 (drawn according to official Manual of Style guidelines)