Nucleophilic and radical addition of H₂S to methyl linolenate and linseed oil

Hydrogen sulfide was added to methyl linolenate and linseed oil to yield mercapto, thio, and thiolan derivatives. Nucleophilic conditions at low temperatures gave faster and more complete reactions than did free radical conditions. Major reaction products were identified by gas liquid chromatography, mass spectrometry, and nuclear magnetic resonance. Nucleophilic addition of hydrogen sulfide to the methyl esters of hydrogenated nonconjugatable linseed oil was made at −70 C in the presence of boron trifluoride, and thiolan derivatives appeared to form in preference to thiane derivatives.