DIPHENYL DISULFIDE

Chemical properties

White to light yellow crystal.

Occurrence

Naturally occurring phytoalexin-like substan

The Uses of DIPHENYL DISULFIDE

Diphenyl disulfide is one of the most popular organic disulfides used in organic synthesis. It is used as a reagent for the α-phenylsulfenylation of carbonyl compounds. It participates in hydrothiolation of alkynes via amine-mediated single electron transfer mechanism. It is the hydrolysis product of dyfonate.

What are the applications of Application

Phenyl disulfide is the hydrolysis product of dyfonate( insecticide ) and participates in hydrothiolation of alkynes via amine-mediated single electron transfer mechanism.

Preparation

By heating and passing a stream of air over an ammoniacal solution of thiophenol.

Definition

ChEBI: Diphenyl disulfide is a member of benzenes.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 35, p. 1770, 1987 DOI: 10.1248/cpb.35.1770
Tetrahedron Letters, 25, p. 703, 1984 DOI: 10.1016/S0040-4039(01)80004-6

Purification Methods

Crystallise the disulfide from MeOH. [Alberti et al. J Am Chem Soc 108 3024 1986]. Also crystallise it repeatedly from hot Et2O, then dry it in a vacuum at 30o over P2O5, fuse it under N2 and re-dry it; the whole procedure being repeated, with a final drying under a vacuum for 24hours. Alternatively, recrystallise it from hexane/EtOH solution. [Burkey & Griller J Am Chem Soc 107 246 1985, Beilstein 6 H 323, 6 IV 1560.]