Sulfur monochloride, with

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 ... 

Sulfurized olefins (S2CI2 plus isobutene) are further reacted with S and Na2S to give products useful as extreme pressure lubricant additives (144,145). The reaction of unsaturated natural oils with sulfur monochloride gives resinous products known as Factice, which are useful as art-gum erasers and mbber additives (146,147). The addition reaction of sulfur monochloride with unsaturated polymers, eg, natural mbber, produces cross-links and thus serves as a means for vulcanizing mbber at moderate temperatures. The photochemical cross-linking of polyethylene has also been reported (148). 

Levinstein A process for making mustard gas, (C1CH2CH2)2S, by reacting sulfur monochloride with ethylene ... 

Although the first report on the reaction of sulfur monochloride with compounds containing active methylene groups had been published more than 120 years ago (1885CB2090), correct structures of the isolated products were proved only 28 years ago (1980CJC1233). The reaction of -dialkyl- and diaryl-malonodiamides 191 with sulfur monochloride gave symmetrically substituted 1,2,4,5-tetrathianes 192 (Scheme 95). 

The reaction of sulfur monochloride with 1,2-epoxide to give /9-chlori-nated symmetrical sulfites [40],... 

Synthesis of sulfur tetrafluoride by fluorination of sulfur monochloride with elemental fluorine in the presence of antimony(III) chloride or phosphorus trichloride as a catalyst has also been reported 22-23 sulfur dichloride, which is formed as the byproduct, is converted back to sulfur monochloride in an absorber filled with granulated sulfur and then recycled. 

One route to thianthrene (70 Z, Z = S) involves reaction of sulfur monochloride with benzene over aluminum chloride (66HC(21-2)1155). 

A general route to phenoxathiins 85 (Z = O, Z = S) utilizes the reaction of diphenyl ethers with sulfur. One route to thianthrene 85 (Z, Z = S) involves reaction of sulfur monochloride with benzene over aluminum chloride. Likewise, tf-methoxyphenol reacts with sulfur dichloride to give, depending on the rate of addition of the reactant, 2,8-dihydroxy-3,7-dimethoxythianthrene 89 or l,6-dichloro-2,7-dihydroxy-3,8-dimethoxythianthrene 90 <1997JCM272>. 

Thus thionyl chloride reacted with either ethylenimine or 2-methyl-aziridine in the presence of triethylamine, which neutralized the hydrochloric acid produced by the reaction. The resulting 1,T-sulfinyldiaziridine and its 2-methyl analog were readily purified by distillation at reduced pressure. Similarly l,T-dithiodiaziridine and l,T-dithiobis(2-methylaziridine) were obtained by reaction of sulfur monochloride with the appropriate aziridine. 

Reaction with 2,4,6-tri-t-butylaniline (1). The reaction of sulfur monochloride with this hindered amine results in formation of two tautomers, (2) and... 

Disulfur pentoxydichloride has also been prepared by treating sulfur monochloride with sulfur trioxide vapor at low temperatures. ... 

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