Organic Disulfides and Related Substances. 45. Synthesis and Properties of Some Disulfide Sulfinate Salts Containing No Nitrogen

Article abstract of DOI:10.1021/je00044a034

Disulfide sulfinates of the structure RSS(CH2)4SO2Na were synthesized by reaction of 1,2-dithiane 1,1-dioxide (1), thiols, and sodium methoxide in methanol.Disproportionation was minimized by precipitating and reprecipitating the products with ether as quickly as possible; where R = aryl, protection from light is advisable.The groups R typify large lipophilic ones (n-decyl, 1-adamantyl), small hydrophilic ones (2-carboxyethyl, 2,3-dihydroxypropyl), disulfide sulfinates <(CH2)nSS(CH2)4SO2Na>, and aryl groups substituted by electron-donating or electron-withdrawing groups.The products usually were quite hygroscopic and were isolated as hydrates.They disproportionated with varying ease in aqueous solution either to 1 or to the two symmetrical disulfides, RSSR and NaO2S(CH2)4SS(CH2)4SO2Na.