Sulfoxides and disulfides from sulfenic acids: Synthesis and applications

Controlled Release of Volatile Enones from Monomeric and Dimeric Thioether, Sulfoxide and Sulfone Profragrances

“…Neither dodecanethiol, obtained either from thioethers or from sulfoxides, nor S-dodecyl dodecane-1sulfinothioate ((�)-15) were found in any of the samples. Because both of them could theoretically generate dodecyl disulfide, either by dimerisation of dodecanethiol under oxidative conditions, [34,67] or by thermal disproportionation of (�)-15, [34,51,52] we analysed the extracted samples for the presence of this compound, which is commercially available. As for the other compounds listed in Table 5, we determined the MS/MS spectra and LC retention time of dodecyl disulfide at higher concentrations as a reference (C 24 H 51 S 2 + , [M + H] + , 403.34267), which ionised only poorly in the MS source.…”

“…In their original work, [7] Fehr and co-workers suggested that thioethers C might be oxidised in air to the corresponding sulfoxides D. [24 -26] According to the literature, these could then theoretically undergo base-catalysed [27,28] or thermal [29 -31] 1,4-elimination to form enones, together with a sulfenic acid E. [32] Sulfenic acids are unstable and give rise to further side products. [33,34] Similarly, if oxidation of the thioethers proceeded to the corresponding sulfone F, 1,4-elimi-nation would yield sulfinic acids G, [27,35] which further react to form additional products. Other mild conditions to generate enones from thioethers through the oxidation to sulfoxides and sulfones, eventually forming β-alkoxy carbonyl compounds by reaction of the intermediate enones with alcohols, have also been described.…”

“…According to the literature, these could then theoretically undergo base‐catalysed [27,28] or thermal [29–31] 1,4‐elimination to form enones, together with a sulfenic acid E [32] . Sulfenic acids are unstable and give rise to further side products [33,34] . Similarly, if oxidation of the thioethers proceeded to the corresponding sulfone F , 1,4‐elimination would yield sulfinic acids G , [27,35] which further react to form additional products.…”