Brintzinger, Herbert published the artcileOrganic sulfur chlorides. VII. Syntheses with α-chloroethylsulfur chloride, Product Details of C4H8Cl2S2, the publication is Chemische Berichte (1954), 300-14, database is CAplus.
cf. C.A. 47, 7433a. Adding 68 g. SO2Cl2 dropwise at -20° to 61.5 g. (EtS)2 in 150 cc. CCl4, adding another 123 g. SO2Cl2 at -15°, warming the mixture to 20°, keeping it overnight, and distilling it give 90% MeCHClSCl (I), b27 38°. Passing CHCH into 13.1 g. I in 50 cc. CCl4 3 h. and distilling the mixture give CHCl:CHSCHClMe, b14 75°, which decompose on standing. Adding dropwise 10.5 g. cyclohexene in 40 cc. CCl4 to 13.5 g. I at 20° gives α-chloroethyl 2-chlorocyclohexyl sulfide (II) which decompose on distillation at 2 mm. Heating II at 150° until HCl is no longer split off and distilling off the volatile part leave a thermoplastic dark brown resin. Adding 6.6 g. cyclopentadiene in 35 cc. CCl4 to 13.1 g. I at below 30° and fractionating the mixture give 4-chlorocyclopenten-2-yl vinyl sulfide, b7 65°, which polymerizes readily when the solvent is distilled off at atm. pressure; on heating it 4 h. at 120° a dark thermoplastic resin is formed. Adding dropwise 10.4 g. styrene in 30 cc. CCl4 to 13.1 g. I at below 25° and distilling the mixture give β-chlorophenethyl vinyl sulfide (III), b8 135°. Heating III 50 h. at 80° gives a thermoplastic styrene soft resin, soluble in chlorinated hydrocarbons. Heating III at 160° until HCl is no longer evolved (50 h.) gives a hard black resin containing 3% Cl. Adding dropwise 26.2 g. I in 10 cc. THF (THF) to 10.4 g. cycloöctatetraene in 20 cc. THF at 20° and distilling off the THF in vacuo give what may be 2,7-dichloro-5,8-bis(α-chloroethylmercapto)bicyclo[0.2.4]oct-3-ene (IV) as a viscous yellow-red oil. Heating IV 18 h. at 100° gives a hard nonthermoplastic polymer, (C12H14Cl2S2)x. When IV is heated 10 h. at 160° a Cl-free nonthermoplastic resin of the composition (C12H12S2)x is obtained. Adding 13.1 g. I slowly at 35° to 6.6 g. CH2(CN)2 in 10 cc. THF causes the evolution of HCl; distilling off the THF in vacuo leaves a red oil which soon polymerizes with the evolution of heat and HCl, giving a soft resin which, on heating 24 h. at 100°, gives a dark brown thermoplastic polymer, (C5H5N2ClS)x. Refluxing 13.1 g. I and 7.4 g. THF 28 h. and distilling the mixture give δ-chlorobutyl α-chloroethanesulfenate, CH2Cl(CH2)3OSCHClMe, b12 88°, decomposing to a red oil after a few days. Adding slowly CH2N2 [from 10 g. MeN(NO)CONH2] to 8.5 g. I and distilling off the ether in vacuo give ClCH2SCHClMe, b1 40°, mobile oil, decomposing on standing at 20°. Shaking 26 g. I 3 h. with 25 g. Hg and warming the decanted solution with fresh Hg 0.5 h. at 50° give (CH2ClCH2S)2, yellow oil, b9 84°. Adding 15 g. I dropwise at 5° to 40 g. dry Me2CO, warming the mixture 0.5 h. at 35°, and fractionating it give hexakis(α-chloroethylmercapto)acetone, b2 70°, which, heated 10 h. at 80°, polymerizes to a hard Cl-free resin. When equal parts of I and Me2CO are mixed, heat and HCl are evolved; the mixture, heated 5 h. at 80° and fractionated, gives hexakis(ethylmercapto)acetone, light yellow oil, b15 53°. Mixing 12 g. PhAc and 13.1 g. I and distilling off the volatile parts in vacuo give a compound, MeCHClSCHBzSCHMeCHBzSCHClMe, which splits off HCl at 20°, completely after heating at 100°, giving a hard resin of the composition (C22H22O2S3)x. Adding 13.1 g. I to 20 g. CH2Ac2 at below 30° and distilling the mixture give 3-(α-chloroethylmercapto)pentane-2,4-dione (V), b1 82°. Shaking 8 g. V with a small excess of 10% KOH 10 min. and adding 150 cc. H2O give (3-vinylmercapto)pentane-2,4-dione, mobile oil, b0.5 70°. Adding 39.3 g. I in 3 portions to 10 g. CH2Ac2, keeping the mixture several hrs., and distilling it give tris(α-chloroethylmercapto)pentane-2,4-dione, b12 104-7°. Similarly, equimolar amounts of I and AcCH2CO2Et give (as primary reaction product) Et α-(α’-chloroethylmercapto)acetoacetate (VI), which, heated 15 h. at 65°, gives Et α-(vinylmercapto)acetoacetate, yellow mobile oil, b18 115°. Adding 39.3 g. I slowly to 7.2 g. MeCOEt at 30° causes a strong evolution of HCl; the mixture is heated several hrs. at 100°, giving a Cl-free polymer, (C20H24OS8)x, as a nonthermoplastic black resin. Similarly, 39.3 g. I and 7 g. MeCOCH: CH2 give MeCOCHClMe, b28 40°, and a resin which, heated 4 h. at 100°, gives a nonthermoplastic insoluble resin of the composition (C14H16OS5)x. Adding 6.5 g. I to 8 g. carbazole in 125 cc. warm xylene, heating the mixture 1.5 h. at 60°, and concentrating the filtered black solution in vacuo give (α-N-carbazolylethyl) (N-carbazolyl) sulfide, yellow crystals, m. 212° (decomposition), and a polymer which is obtained as the main product when 8 g. carbazole and 6.5 g. I are refluxed in 125 cc. xylene 2.5 h., the cooled solution is filtered, concentrated, filtered again, and evaporated, the residue extracted with CCl4, and the residue of the CCl4 extract heated 1 h. at 80°/12 mm. Adding dropwise 6.5 g. I in 15 cc. AcOH to 12.1 g. PhNMe2 in 15 cc. AcOH, stirring the mixture 1 h. at 35°, adding 22.5 g. KOH in 200 cc. H2O, extracting with ether, distilling off the PhNMe2 from the residue of the dried ether extract, and recrystallizing the residue 3 times from EtOH give [α-(4-dimethylaminophenyl)ethyl] 4-dimethylaminophenyl sulfide, yellow needles, m. 125°. Adding in small portions with cooling 30 g. AlCl3 to 13.1 g. I in 100 cc. C6H6, keeping the mixture overnight, distilling off about 50 cc. C6H6, pouring the residue into iced HCl, extracting with ether, and distilling the washed (NaOH) and dried organic solution at 30°/10 mm. leave Ph α-phenethyl sulfide, yellow crystals, m. 161°. Treating 11.4 g. CO(NHPh)2 in 250 cc. CHCl3 several hrs. with 13.1 g. I and distilling off the CHCl3 give N,N’-diphenyl-N,N’-bis(α-chloroethylmercapto)thiourea-2HCl, m. 132°. Adding 13.1 g. I to 22.8 g. CO(NHPh)2 in 120 cc. THF and distilling off the THF leave a viscous yellow soft resin which is heated 1 h. at 60°/12 mm. and has the composition (C15H16N2Cl2S2)x, soluble in CCl4 and ether, and giving a clear solid film. Adding dropwise 13.1 g. I to 21.1 g. diphenylguanidine in 200 cc. CHCl3 and distilling off the CHCl3 give a polymer, (C15H17N3Cl2S)x, as a tough thermoplastic film-forming red resin. Adding 13.1 g. I to 9.8 g. cyclohexanone in 50 cc. CCl4 at below 40°, keeping the mixture 48 h. at 20°, and fractionating the solution give a colorless Cl-containing oil, b8 45°, which readily decompose, giving a Cl-containing dark red soft resin. When I and cyclohexanone are mixed without cooling, the mixture is heated 20 h. on a water bath, and the volatile portion is distilled off a red thermoplastic hard resin of the composition (C8H12OS)x is obtained. Treating 9.4 g. PhOH in 50 cc. CHCl3 with 13.1 g. I, distilling off the CHCl3, and heating the residue 5 h. at 60° give a soft resin, containing 12.4% Cl, which after heating another 5 h. at 100° gives a Cl-free hard resin of the composition (C8H9OS)x.
Chemische Berichte 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, Product Details of C4H8Cl2S2.
Referemce:
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