Fuson, Reynold C. published the artcileLevinstein mustard gas. I. 2-Haloalkylsulfenyl halides, SDS of cas: 1002-41-1, the publication is Journal of Organic Chemistry (1946), 469-74, database is CAplus and MEDLINE.
In the reaction mechanism postulated by Conant, et al. ( C.A. 14, 1677), ClCH2CH2SCl (I) is suggested as an intermediate in the formation of (ClCH2CH2)2S (II) although I has never been obtained in a pure state. When 169 g. Cl is passed into 453 g. (ClCH2CH2)2S2 (III) in dry CCl4 at such a rate that the temperature does not exceed 10° the solvent distilled off, and the residue fractionated, 57-79% I, b15 47-7.5° nD20 1.5290, is obtained. I, orange liquid, is moderately stable when kept in a brown bottle in the refrigerator. The residue (173 g.) from the distillation, on further fractionation, gives III and a new compound, C4H7Cl3S2, yellow liquid, nD21.8 1.5768. When I is treated with KI, III is formed with liberation of iodine. When I is treated with H2O, III, b2 83-8°, nD20 1.5670, m. 1° is formed, in addition to an unidentified product, probably the thiosulfonic ester. When equal mols. I and S are heated for 3 h. at 60-5° and distilled, S2Cl2, III and (ClCH2CH2)2S3 (IV) are obtained. Oxidation of 4.8 g. I with 30 cc. HNO3 (d. 1.42) on a steam bath, evaporation to dryness, dissolution of the residue in an excess of NH4OH, and evaporation again give 79% ClCH2CH2SO2ONH4, m. 191-3°. When CH2:CH2 is passed into 10 g. I in 90 cc. CCl4, the solution is decolorized with formation of 70% II, b1 54-5°, nD20 1.5281. I and cydohexene (V) give 69% 2-chlorocyclohexyl 2-chloroethyl sulfide (VI), b0.2 84-6° (p-tolylsulfonylsulfilimine, prepared by treating VI with Chloramine-T, m. 145.5-6° (preheated bath)). When 185 g. I is dropped into 1500 cc. AcOEt over a period of 2 h. saturated with CHCH at 0° with continuous introduction of CHCH, 56% 2-chloroethyl 2-chlorovinyl sulfide, b0.15 30°, b0.75 46°, m. -24° nD20 1.5480 (p-tolylsulfonylsulfilimine m. 105-5.5° sulfone, platelets from petr. ether, m. 37.5-8°), is obtained. When 35 g. I and Me2CO are allowed to react, HCl is evolved and the solution becomes colorless, giving acetonyl 2-chloroethyl sulfide, b0.75 76-85° (semicarbazone m. 145-6°). When I and piperazine are allowed to react according to Rheinboldt and Mott (C.A. 33, 4959.4), 1,4-bis(2-chloroethylmercapto)piperazine, needles from EtOH, m. 117-18° is obtained. When III is treated with Br in 150 cc. CCl4, ClCH2CH2SBr is obtained after distilling off the solvent in vacuo at room temperature It decomposes on distillation at 3 mm. When V is added to the bromination reaction mixture, 75% 2-bromocyclohexyl 2-chloroethyl sulfide is formed, decomposing slightly on distillation at 0.35 mm. (p-tolylsulfonylsulfilimine, crystals from EtOH, m. 145-6°).
Journal of Organic Chemistry published new progress about 1002-41-1. 1002-41-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 1,2-Bis(2-chloroethyl)disulfane, and the molecular formula is C4H8Cl2S2, SDS of cas: 1002-41-1.
Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics