Benati, L.; Tiecco, M.; Tundo, A. published an article in 1963, the title of the article was Homolytic reactions. VII. Benzyl aryl sulfides.Synthetic Route of 53136-21-3 And the article contains the following content:
cf. CA 58, 13830c; 59, 6293f. By heating benzyl aryl sulfides and tert-butyl peroxide, meso- and dl-1,2-bis(arylthio)-1,2-diphenylethanes were obtained: their configurations were established through trans elimination of thiophenol and synthesis from erythro and threo-1-chloro-2arylthio-1,2-diphenylethanes and thiophenates, p-XC6H4SCH2Ph (I) (X = Br) (II) (9 g.), and 50 ml. tert-butyl peroxide (III) refluxed 10 hrs. and cooled gave 1.8 g. meso-(p-XC6H4SCHPh)2 (meso-IV) (X = Br) (V), m. 223°; the mother liquor chromatographed on Al2O3 yielded 3.3 g. II, m. 64°, 0.6 g. V, and 1.5 g. dl-IV (X = Br) (VI), m. 125-6° (EtOH). V was also obtained from erythro-1-(p-bromophenylthio)-2-chloro-1,2-diphenylethane and p-BrC6H4SNa (VII), and V. was also obtained from threo-1-(p-bromophenylthio)-2-chloro-1,2-diphenylethane with VII. Similarly, 9 g. I (X = Cl) and 50 ml. III gave 2.4 g. meso-IV (X = Cl), m. 209-10°, and 1.6 g. dl-IV (X = Cl), m. 121-2°. I (X = H) (10 g.) furnished meso-IV (X = H), m. 193-4° (EtOH), and 1.8 g. dl-IV (X = H), m. 119-20°. V (1 g.) in 200 ml. tetrahydrofuran (THF) was treated 15 hrs. with NaNH2 prepared from 0.87 g. Na and 500 ml. NH3, evaporated, diluted with Et2O and H2O to give 0.6 g. V; the Et2O residue dissolved in AcOH, filtered, treated with H2O2 1 hr. on a water bath, cooled, and diluted with H2O gave some cis-1-(p-bromophenylsulfonyl)stilbene, m. 194-6°. VI (0.5 g.) in 100 ml. THF treated 15 hrs. with NaNH2 (prepared from 0.12 g. Na and 250 ml. NH3), evaporated, diluted with Et2O and H2O, Et2O evaporated, and the residue chromatographed on Al2O3 gave 0.2 g. trans-pbromophenylthiostilbene, m. 92-3°, and 0.2 g. VI. transStilbene (10 g.) in 250 ml. anhydrous CHCl3 treated with 10 g. pBrC6H4SCl in 50 ml. CHCl3 gave erythro-1-(p-bromophenylthio)-2-chloro-1,2-diphenylethane (VIII), m. 145-7° (C6H6-ligroine). VIII (8.1 g.) in 300 ml. Et2O treated 10 hrs. with NaNH2 (prepared from 1.4 g. Na and 500 ml. NH3) and worked up furnished 2.6 g. cis-1-(p-bromophenylthio)stilbene (IX), m. 104-5°. IX (1 g.) in Et2O treated with NaNH2 yielded, after treatment with H2O2, trans-1-(p-bromophenylsulfonyl)stilbene, m. 146-7°. Cis-stilbene and p-BrC6H4SCl furnished threo-1(p-bromophenylthio)-2-chloro-1,2-diphenylethane (X), m. 702° (ligroine). X and NaNH2 in NH3 yielded 95% trans-1-(pbromophenylthio)stilbene, m. 92-3°. VIII (1 g.) in 90 ml. 80% EtOH and 75 ml. dioxane treated 4 hrs. at 50° with pBrC6H4SNa (XI) (prepared from 0.5 g. p-BrC6H4SH and 0.06 g. Na in 10 ml. EtOH) gave V. X treated as above with XI furnished VI. The experimental process involved the reaction of Benzyl(4-bromophenyl)sulfane(cas: 53136-21-3).Synthetic Route of 53136-21-3
Benzyl(4-bromophenyl)sulfane(cas:53136-21-3) belongs to ethers. Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however. Synthetic Route of 53136-21-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem