Hydrogen Sulfide Adducts of Methyl Oleate and Linoleate

Sulfur compounds derived from photochemical addition of hydrogen sulfide to methyl oleate and linoleate were separated by preparative gas chromatography. The major compounds were investigated by NMR, mass and IR spectroscopy and by elemental analysis. The primary product of the methyl oleate reaction was methyl 9(10)-mercaptostearate. Gas chromatograms of the product from methyl linoleate showed four principal peaks. From mass spectra and NMR data, we identified methyl 9-(2-pentyl-1-thiolan-5-yl)nonanoate, methyl 8-(2-hexyl-1-thiolan-5-yl)octanoate and methyl 9-(3-hexyl-1,2-dithiolan-5-yl)nonanoate. Evidence for the formation of methyl mercapto-octadecenoates and methyl dimercaptostearates was also obtained.