Styrene oxide reaction with ethanethiol

Reaction of styrene oxide with sodium ethanethiolate completes the synthesis. 

The latter reaction sequence was of importance since addition of the thiol glutathione to arene-oxide intermediates under control of hepatic glutathione-S-epoxide transferase enzyme(s) is a very important metabolic transformation. It would appear probable that most of the structures of the arene oxide-glutathione adducts (premercapturic acids) reported in the literature before 1975 are incorrect with respect to the position of the hydroxy and thioether substituents (they should now be reversed). Addition of thiomethoxide anion to arene oxide 70 may occur via 1,6- and 1,4-addition, although one of these thioether adducts could also be accounted for by the alternative arene-oxide intermediate obtained from an oxygen-walk. Styrene 3,4-oxide (S3) has been observed to react with ethanethiol to yield three adducts which appear to aromatize to three isomeric ethylthiostyrenes without the formation of episulphonium intermediates. ... 

Alkyl Bound to Miscellaneous Elements. Several compounds in which alkyl is bound to a sulfur atom have become quite important in recent years for example, the mercaptans, such as amyl and ethyl mercaptan, are used as warning agents in natural gas because of their intense and disagreeable odor. Mercaptans are also employed in organic syntheses as, for instance, the manufacture of sulfonal by the condensation of ethyl mercaptan (ethanethiol) with acetone, followed by oxidation. In recent years a very considerable amount of mercaptan has been used for controlling the polymerization reaction between butadiene and styrene to form synthetic rubber (GR-S). 

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See also in sourсe #XX -- [ ]

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