Degani, Jacopo; Tiecco, Marcello; Tundo, Antonio published an article in 1962, the title of the article was Homolytic reactions. VI. Reactions between diaryl disulfides and benzyl radicals.Electric Literature of 53136-21-3 And the article contains the following content:
cf. ibid. 1204; CA 56, 5870f. The reactions of diaryl disufides, XC6H4SSC6H4X (I), with PhCH2+ (II) are studied, II being prepared by the addition of 29 g. tert-butyl peroxide to a toluene (150 ml.) solution of I and refluxing 24 hrs. Thus, 14.3 g. I (X = Cl) and II yielded (by chromatography on Al2O3, eluting with petroleum ether) traces of p-ClC6H4SMe, identified as its sulfone, m. 96°, and of diphenylethane, m. 52°, 3.3 g. p-ClC6H4SCH2Ph, m. 52-3°, and 0.5 g. oil from which further chromatographic separation yielded α-(p-chlorophenylthio)diphenylethane, m. 46°, (p-ClC6H4S)2CH2, m. 43-4°, (p-ClC6H4S)2CHPh, m. 60-1°, and unreacted I. Elution with ligroine yielded 0.2 g. unknown compound, m. 77°, 0.3 g. (p-ClC6H4SCHPh)2 m. 210-11°. and 0.15 g. of another unknown compound, m. 120°. Elution with 1:1 ligroine-C6H6, followed by C6H6, yielded tars; elution with CHCl3 yielded 0.25 g. p-C6H4SOCH2Ph, m. 135°. The reaction of 10 g. I (X = H) and II yielded traces of Ph2CH2, thioanisole (sulfone m. 80-1°), 5.2 g. benzyl phenyl sulfide, m. 40-1°, little (PhS)2CH2, m. 40°, Ph2CHPh, m. 52° α-phenylthiodiphenylethane, and an unidentified S compound, m. 60-6° later, (PhCHSCPh)2, m. 194° and benzyl phenyl sulfoxide, m. 124°, and another unknown compound m. 101-3° were recovered. With 18.5 g. I (X = Br) and II, the products separated were (PhCH2)2, m. 52°, p-bromothioanisole, m. 37-8°, 4.6 g. p-BrC6H4SCH2Ph, m. 64°, a little α-(p-bromophenylthio)diphenylethane, m. 66° p-BrC6H4SCH2SC6H4Br, m. 77°, (p-BrC6H4S)2CHPh, m. 79-80% an unidentified S compound, m. 135-6°, and p-bromophenyl benzyl sulfoxide, m. 141-2°. Starting with 11.3 g. p-chlorobenzyl phenyl sulfide and II, the reaction products yielded 1.1 g. α-(p-chlorophenylthio)diphenylethane, m. 46°, 0.3 g. (p-ClC6H4SCHPh)2, m. 210-11°, and traces of an identified compound, m. 120% also obtained from I (X = Cl). Refluxing 12 g. p-ClC6H4SMe in 120 ml. ClPh with 21.2 g. tert-butyl peroxide 24 hrs. yielded (p-ClC6H4S)2CH2, m. 43-4°, (p-ClC6H4SCH2)2, m. 94°, an unknown compound, m. 77°, and tars. Also prepared were α-phenylthiodiphenylethane, m. 148° (by refluxing in alc. the Na derivative of PhSH and α-chlorodiphenylethane 1 hr.); α-(p-bromophenylthio)diphenylethane, prisms, m. 66° (ligroine); and α-(p-chlorophenylthio)diphenylethane, prisms, m. 46° (ligroine), by analogous methods. It is concluded that the diaryl disulfides react with the benzyl radicals forming first thioanisoles and benzyl aryl sulfides, which react in turn to form a variety of other sulfur derivatives The experimental process involved the reaction of Benzyl(4-bromophenyl)sulfane(cas: 53136-21-3).Electric Literature 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. Electric Literature of 53136-21-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem