Sulfur disulfur dichloride

Chloroethyldisulfides are obtained by electrophilic attack on the sulfur atom of thiiranes by sulfenyl halides (Scheme 39). Sulfur dichloride and disulfur dichloride react similarly to give more sulfur-rich derivatives di- and tri-sulfenyl halides, and tri- and tetra-sulfides (Scheme 42). A 1 1 ratio of sulfur halide to thiirane gives the di- or tri-sulfenyl halide a 2 1 ratio the tri- or tetra-sulfide. Thiirane 1-oxides are cleaved by sulfenyl halides to thiolsulfinates (Scheme 43) (74JAP7440461). 

One of the products of the reaction of sulfur with chlorine is disulfur dichloride, S2C12, a yellow liquid with a nauseating smell it is used for the vulcanization of rubber. When disulfur dichloride reacts with more chlorine in the presence of iron(III) chloride as a catalyst, the foul-smelling red liquid sulfur dichloride, SC12, is produced. Sulfur dichloride reacts with ethene to give mustard gas (16), which has been used in chemical warfare. Mustard gas causes blisters, discharges from the nose, and vomiting it also destroys the cornea of the eye. All in all, it is easy to see why ancient civilizations associated sulfur with the underworld. 

In absence of diluent or other effective control of reaction rate, the sulfoxide reacts violently or explosively with the following acetyl chloride, benzenesul-fonyl chloride, cyanuric chloride, phosphorus trichloride, phosphoryl chloride, tetrachlorosilane, sulfur dichloride, disulfur dichloride, sulfuryl chloride or thionyl chloride [1], These violent reactions are explained in terms of exothermic polymerisation of formaldehyde produced under a variety of conditions by interaction of the sulfoxide with reactive halides, acidic or basic reagents [2], Oxalyl chloride reacts explosively with DMSO at ambient temperature, but controllably in dichloromethane at -60°C [3]. 

Diselenium dichloride and seleninyl chloride both explode on addition of potassium [1,3], while the metal ignites in contact with phosphorus trichloride vapour or liquid [2], Mixtures of potassium with sulfur dichloride or sulfur dibromide, phosphorus tribromide or phosphorus trichloride, and with phosgene are shock-sensitive, usually exploding violently on impact. Potassium also explodes violently on heating with disulfur dichloride, and with sulfur dichloride or seleninyl bromide without heating [3]. 

They have been several recent investigations of the reactions of disulfur dichloride with other organic substrates. Rokach and co-workers37 have found that 2-aminoacetamides afford 2-substituted l,2,5-thiadiazol-3(2J7)-ones (33). This illustrates a frequent facet of such reactions the elision of the second sulfur atom. A similar reaction, with loss of a sulfur atom, occurs with 2-alkylaminophenyl acetamides.38... 

The effect of initiators (diluted sulfuric acid, chlorine dioxide, sulfur dioxide or disulfur dichloride) on ignition of mixtures of barium, lead or potassium chlorates with sulfur was examined [1] Presence of copper ion or metal (e.g. from a sieve) may also lead to explosion of such mixtures [2], A review of hazards of sulphur/chlorate mixtures in the firework industry has been published [3],... 

The product 303 from disulfur dichloride and 2,3-dimethylbuta-l,3-diene rearranges spontaneously to the tetrahydrothiophene 304 (equation 159)150. The reaction of liquid sulfur dioxide with conjugated dienes 305 (e.g. butadiene, isoprene) results in cyclic sulfones which dissociate into their components on heating (equation 160)151 152. 

Synonyms Sulfur chloride sulfur subchloride disulfur dichloride... 

Industrially the curing (vulcanization) of diene homopolymers and copolymers with elementary sulfur is carried out in a heated press at 100-140 °C (hot curing) this cannot be done in a normal laboratory on account of the expensive apparatus required. However, the principle of curing can be illustrated by crosslinking a butadiene-styrene copolymer (SBR 1500) with disulfur dichloride (SjCy at room temperature (cold curing) ... 

Synonyms disulfur dichloride sulfur subchloride sulfur monochloride... 

The compound decomposes above 140°C to form sulfur dioxide, chlorine and disulfur dichloride ... 

When deprotonated dimethyl sulfone is reacted with 2 equiv of benzonitrile, compound 109 is obtained in low yield (Equation 91) <1973JOM(59)53>. Compounds of the general structure 179 can be prepared from two molecules of enamino esters 288 and sulfur dichloride or disulfur dichloride <1984JOG4780> or in low yield using chlorocarbo-nylsulfenyl chloride 289 as the source of sulfur <1985JHC1621> (Equation 92). A series of cycloadditions lead to the formation of 131 from 290 and two molecules of the ynamine 291 (Scheme 69) <1995LA1795>. 

Bis(2-chloroethyl) ether (4) reacts with sulfur tetrafluoride, hydrogen fluoride and ca. 3 % disulfur dichloride (in relation to the ether) to give, depending on the reaction temperature, dichlorotrifluoro ether 5, chlorotetrafluoro ether 6, or pentafluoro ether 2.238... 

The reaction of acetone with sulfur tetrafluoride, hydrogen fluoride and a catalytic amount of disulfur dichloride gives, instead of 2,2-difluoropropane, polyfluorodipropyl sulfides 8, 9, or disulfide 10 in which the number of fluorine atoms depends on the reaction temperature. The same products are obtained when 2,2-difiuoropropane, a product of the replacement of the carbonyl group of acetone by fluorines, is treated with the same reagent (SF4/HF/S2C12).239... 

Similarly, butan-2-one, pentan-3-one, 2,2-difluorobutane and 3,3-difluoropentane can be converted by the sulfur tetrafluoride/hydrogen fluoride/disulfur dichloride system into fluoro sulfides and fluoro disulfides.240... 

Disulfides are also formed in reactions of alkenes or secondary alcohols with the sulfur tetrafluoride/hydrogen fluoride/disulfur dichloride system under mild conditions. At elevated... 

One of the products of the reaction of sulfur with chlorine is disulfur dichloride, S2C12, a yellow liquid with a nauseating smell it is used for the... 

Reaction of oxime 34 with disulfur dichloride yielded 35 <1997BSB605> which formally was derived from two molecules of oxime and one sulfur atom (Equation 6). 

Amidines dissolved in dichloromethane at 0°C and under an atmosphere of nitrogen can be in combined with sulfur dichloride (SC12) or disulfur dichloride (S2C12) to easily generate the dithiadiazolium chlorides. Equation (6) illustrates the overall transformation to give 4-phenyl-l,2,3,5-dithiadiazolium chloride 23. Since HC1 is generated... 

For the preparation of this compound the reaction between ammonia and disulfur dichloride, S2CI2, is employed. Besides tetrasulfur tetranitride, sulfimide, S7NH, some sulfur, and ammonium chloride also are formed. 

Passing chlorine gas through molten sulfur produces liquid disulfur dichloride. How many molecules of chlorine react to produce 50.0 g of disulfur dichloride ... 

Sulfur groups at lower oxidation level can also be substituted into indoles and pyrroles. Disulfur dichloride, for example, reacts with 3,4-diethylpyrrole to produce 12-membered ring compound 73 <2005CC2122>. Reaction with 2,5-dichloropyrrole (no free -positions) formed a ring across carbons C(3) and C(4) giving 74 <2003ARB161 >. Reaction of /V-mcthylindolc also produced a pentathiepin, across the 2- and 3-positions. 

The [S + C=C] route is illustrated by reaction of disulfur dichloride or sulfur dichloride with alkynes (Scheme 9), or by episulfidation of alkenes by sulfur atom donors in the presence of molybdenum oxocomplexes (Scheme 10) . 2-Phenylthiirane is the most efficient sulfur donor in the molybdenum-catalyzed episulfidation and the reaction proceeds stereoselectively as yy/z-addition e.g., the episulfidation reaction of trans-cyclooctene affords /r my-epithiocyclooctane (Scheme 10) <2003JA3871>. 

Thiadiazoles. An acyclic NCCN system in which the NC links may be sp, sp2, or sp3 hybridized reacts with sulfur monochloride or sulfur dichloride to form the appropriate 1,2,5-thiadiazole <1968AHC(9)107, CHEC-111(5.09.9.1.5)545>. Aliphatic 1,2-diamines can be converted into 1,2,5-thiadiazoles using various sulfur sources such as tetrasulfur tetranitride, disulfur dichloride, sulfur dichloride, thionyl chloride, and V(V-ditosylsulfur diimide. Thus, l,2,5-thiadiazole-3,4-dicarbonitrile 555 is prepared from diaminomaleonitrile 554 using neat excess thionyl chloride (Scheme 250) <1995SR299>. 

Amidines react with sulfur dichloride or disulfur dichloride in the presence of base to produce the dithiadiazolium chlorides, as illustrated by the preparation of 4-phenyl-l,2,3,5-dithiadiazolium chloride 763 (Scheme 329) <1989CC1134, CHEC-III(6.11.8.1)507>. 

Probably the best way3 of storing tetrasulfur tetranitride is as the crude product obtained by the procedure described by M. Villena-Blanco and W. L. Jolly1 but with the omission of the chlorination step which converts disulfur dichloride to sulfur dichloride. The total yield of tetrasulfur tetranitride is thereby reduced by a factor of two 1 the crude product contains... 

Upon addition of catalytic amounts of disulfur dichloride, aliphatic ketones react with sulfur tetrafluoride to yield polyfluoro sulfides and disulfides. - In the case of acetone, different products can be isolated depending on the reaction temperature. 

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