Sulfur monochloride, polysulfides

Numerous organic reactions of sulfur monochloride are of practical and commercial importance. Of particular importance is the reaction of sulfur monochloride with olefins to yield various types of addition products (142). With ethylene, the severe vesicant bis(2-chloroethyl) sulfide [505-60-2] (mustard gas) forms with elemental sulfur and polysulfides (see Chemicals IN war). Propylene reacts similarly ... 

A reaction of dithiadiazocanes 234 with sulfur monochloride gave a novel macrocyclic polysulfide, 1,2,3,5,7-pentathiocanes 235, in moderate-to-high yields (2002CL90). The NMR monitoring of this reaction suggested that a plausible route involved the formation of an oxidative transannular S-S bond in a thermally stable secondary species, a symmetrical dithiadication 236, followed by... 

Shipment and. Storage, Sulfur monochloride is minimally corrosive to carbon steel and iron when dry. If it is necessary to avoid discoloration caused by iron sulfide formation or chloride stress cracking, 310 stainless steel should be used. Sulfur monochloride is shipped in tank cars, tank trucks, and steel drums. When wet, it behaves like hydrochloric acid and attacks steel, cast iron, aluminum, stainless steels, copper and copper alloys, and many nickel-based materials. Alloys of 62 Ni—28 Mo and 54 Ni—15 Cr—16 Mo are useful under these conditions. Under DOT HM-181 sulfur monochloride is classified as a Poison Inhalation Hazard (PIH) Zone B, as well as a Corrosive Material (DOT Hazard Class B). Shipment information is available (140). Uses, The reaction of S-CL with aromatic compounds can yield disulfides or mixtures of mono-, di-, and polysulfides. 

The reaction of fluoro- or chlorofluoroalkenes with the sulfur tetrafluoride/hydrogen fluoride/ sulfur monochloride system leads to perfluoroalkanesulfenyl chlorides, (sulfanyl)sulfenyl chlorides, sulfides and polysulfides. Tetrafluoroethene reacts with sulfur tetrafluoride/hydrogen fluoride in the presence of 1 equivalent of sulfur monochloride at 80°C to yield a mixture of pentafluoroethanesulfenyl chloride (4), (pentafluoroethanesulfanyl)sulfenyl chloride... 

TP here are very few examples in the literature of poly (arylene polysulfides). Perhaps the first such preparation was that of Fried el and Crafts (I), in which benzene reacted with sulfur in the presence of aluminum chloride. Within the last 15 years, several poly(arylene polysulfides) have been prepared by related reactions in which various aromatic compounds reacted with sulfur monochloride in the presence of Friedel-Crafts catalysts (2, 3, 4). A variation of this reaction has also been reported using a bifiunctional sulfenyl chloride (5) ... 

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