102780-39-2Relevant academic research and scientific papers
Thiono and Dithio Esters, 42. - Reactions of Thiooxalates with C- and S-Nucleophiles
Hartke, Klaus,Gillmann, Thomas
, p. 1718 - 1727 (2007/10/02)
O,O'-Dimethyl dithiooxalate (1) and dimethyl tetrathiooxalate (2) react with several carbanionic reagents by thiophilic attack to form addition products, which upon hydrolysis yield derivatives 7 and 10 of thioacetic acid having a thioacetal function in the 2-position. 1 is reduced by sodium benzylsulfide to give the E- and Z-enedithiolates 15 and 16.The anion 18 of O-methyl methoxy(methylthio)thioacetate (7a) reacts with allyl and propargyl bromide primarily at the sulfur atom.These products 19, 21 then undergo rearrangements of the Thio-Claisen type to give 20, 22.Oxidation of 18 with iodine yields the methyl dithionosuccinate 26 as a mixture of diastereomers.
