Electrosynthesis of sulfur-containing organic compounds from allene derivatives using a sacrificial mixed sulfur/graphite electrode

Abstract

Electrosynthesis of sulfur-containing organic compounds from aliene derivatives was studied using a sacrificial mixture sulfur/graphite electrode. 1,3-bis(methoxycarbonyl)propadiene ( 1a), 1,1,-diphenyl-3-ethoxycarbonyl-1, 2-butadiene ( 1b), 1,3-diphenylpropadiene ( 1c), and 1-(p-methoxyphenyl)-1,2-butadiene ( 1d) were used as allenes. With la, 6-membered ring compounds with 2S atoms such as dihydrodithiin ( 2a) and dithiin ( 3a) and a dimer bridged with 2S atoms ( 4a) were obtained and their yields were largely dependent on the kind of proton donors used. On the other hand, 1b afforded a 5-membered ring compound with 3S atoms such as 1,2,3-tirthiolane ( 5b) different from the case of 1a. All products will be initiated by the addition of the polysulfide anion produced by electroeduction of elemental sulfur. With 1c and 1d, sulfur-containing organic compounds were not produced.