Sodium 1,3-dithiole-2-thione-4,5-dithiolate


Sodium 1,3-dithiole-2-thione-4,5-dithiolate is the organosulfur compound with the formula Na2C3S5, abbreviated Na2dmit. It is the sodium salt of the conjugate base of the 1,3-dithiole-2-thione-4,5-dithiol. The salt is a precursor to dithiolene complexes and tetrathiafulvalenes.
Reduction of carbon disulfide with sodium affords sodium 1,3-dithiole-2-thione-4,5-dithiolate together with sodium trithiocarbonate:
Before the characterization of dmit2-, reduction of CS2 was thought to give tetrathiooxalate.
The dianion C3S52- is purified as the tetraethylammonium salt of the zincate complex 2-. This salt converts to the bis upon treatment with benzoyl chloride:
Cleavage of the thioester with sodium methoxide gives sodium 1,3-dithiole-2-thione-4,5-dithiolate:
File:DOQXOW.png|thumb|left|Structure of 2-.
Na2dmit undergoes S-alkylation. Heating solutions of Na2dmit gives the isomeric 1,2-dithioledithiolate.