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Electrochemical Reduction of Aromatic Dithio and Thiol Esters
Falsig, Mogens,Lund, Henning
, p. 585 - 590 (2007/10/02)
Electrochemical reduction of benzenecarbodithioic esters (1a-e) and carbothioic S-esters (2a-e) in aprotic medium yields diphenylacetylene; in the presence of an alkylating agent 1 forms a dithioacetal.Cyclic volttammetry shows that the heterogeneous electron transfer is quasireversible; it is followed by a relatively slow dimerization of the anion radicals.In the steps following the dimerization dithiobenzil is formed and 1 acts as a thioacylating agent. 2 behaves analogously to 1, but the follow-up reaction is faster.
