Electrochemical Synthesis of Tetraethylammonium Tetrathiooxalate

Submitted by JONATHAN G. BREITZER, GEOFFREY A. HOLLOWAY, THOMAS B. RAUCHFUSS, and MICHAEL R. SALATA Checked by CHEE LEONG KEE and YAW KAI YAN  

Tetrathiooxalate was originally claimed to result from the reduction of CS2 with sodium. It was eventually shown that the reaction of concentrated solutions of CS2 with Na metal gives the heterocycle 385 , commonly referred to as dmit Isotopic labeling smdies have since shown that 385 arises from the condensation of 384 with C82 according to the equation 284 -I- C82 0385 -1-8.  

To a 150 mL beaker are added a Teflon -coated stir bar and enough merciuy to cover the bottom of the beaker (about 100 g). A saturated solution of Et4NBr (20 g) in acetonitrile (200 mL) is prepared in advance, and llOmL of this solution is added to the beaker followed by C82 (3.3 mL, 0.055 mol). A paper Soxhlet shell 

Department of Chemistry, University of Illinois at T Trhana-Champaign, Urbana, IL 61801. Fayetteville State University, Fayetteville, NC 28301. 

The cmde product is extracted into degassed, deionized water (about 16-20 mL). This deep orange extract is filtered to remove a small quantity of brown solid, and the solid is washed with a minimal volume of water and the washings added to the filtrate. The solution is transferred to a 250 mL round-bottomed flask (alternatively, and even better, the filtration can be done directly into the round- 

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