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Properties of substance:

1,2-bis(p-tolylthio)ethane

Synonyms:

1,2-bis-(p-tolylmercapto)ethane

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C16H18S2

Structural formula as text:

CH3C6H4SCH2CH2SC6H4CH3

Synthesis 1:

Reference: Bordwell, F. G., Pitt, B. M. The Formation of α-Chloro Sulfides from Sulfides and from Sulfoxides / Journal of the American Chemical Society. - 1955. - Vol. 77, No. 3 pp. 576 [doi: 10.1021/ja01608a016]

2C6H5SCH2Cl + Mg → C6H5SCH2CH2SC6H4CH + MgCl2

Addition of 2.4 g. of p-tolyl chloromethyl sulfide in 20 ml. of dry ether to 1 g. of magnesium and a crystal of iodine resulted in a rapid exothermic reaction. The mixture was maintained at reflux for one hour and hydrolyzed with dilute hydrochloric acid. The ether layer was dried over anhydrous potassium carbonate, the ether evaporated and the product crystallized from hexane. In this manner 0.5 g. (26%) of 1,2-bis-(p-tolylmercapto)ethane, m.p. 78—79°, was obtained.

When similarly treated with magnesium, chloromethyl methyl sulfide, chloromethyl t-butyl sulfide and ?-chlorobenzyl methyl sulfide failed to show any reaction.

References:


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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru