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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 
Na2dmit undergoes S-alkylation.{{cite journal, authors=Niels Svenstrup, Jan Becher, title=The Organic Chemistry of 1,3-Dithiole-2-thione-4,5-dithiolate (DMIT), journal=Synthesis, year=1995, volume=1995, issue=3, pages=215–235, doi=10.1055/s-1995-3910 Heating solutions of Na2dmit gives the isomeric 1,2-dithioledithiolate.
tetrathiafulvalene
Tetrathiafulvalene is an organosulfur compound with the formula (. Studies on this heterocyclic compound contributed to the development of molecular electronics. TTF is related to the hydrocarbon fulvalene, , by replacement of four CH groups w ...
s.
Reduction of carbon disulfide
Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical n ...
with sodium affords sodium 1,3-dithiole-2-thione-4,5-dithiolate together with sodium trithiocarbonate Thiocarbonate describes a family of anions with the general chemical formula (''x'' = 0, 1, or 2):
*for ''x'' = 2 it is monothiocarbonate ion
*for ''x'' = 1 it is dithiocarbonate ion
*for ''x'' = 0 it is trithiocarbonate ion
Like the carbonate d ...
:
: 4 Na + 4 CS2 → Na2C3S5 + Na2CS3
Before the characterization of dmit2-, reduction of CS2 was thought to give tetrathiooxalate (Na2C2S4).
The dianion C3S52- is purified as the tetraethylammonium
Tetraethylammonium (TEA), () or (Et4N+) is a quaternary ammonium cation consisting of four ethyl groups attached to a central nitrogen atom, and is positively charged. It is a counterion used in the research laboratory to prepare lipophilic salts ...
salt of the zincate complex n(C3S5)2sup>2-. This salt converts to the bis(thioester) upon treatment with benzoyl chloride
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula . It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring () with an acyl chloride () substituent. It is ...
:
: (C2H5)4sub>2 n(C3S5)2 + 4 C6H5COCl → 2 C3S3(SC(O)C6H5)2 + (C2H5)4sub>2 nCl4Cleavage of the thioester with sodium methoxide
Sodium methoxide is the simplest sodium alkoxide. With the formula , it is a white solid, which is formed by the deprotonation of methanol. Itis a widely used reagent in industry and the laboratory. It is also a dangerously caustic base.
P ...
gives sodium 1,3-dithiole-2-thione-4,5-dithiolate:
: C3S3(SC(O)C6H5)2 + 2 NaOCH3 → Na2C3S5 + 2 C6H5CO2Me
Na2dmit undergoes S-alkylation.{{cite journal, authors=Niels Svenstrup, Jan Becher, title=The Organic Chemistry of 1,3-Dithiole-2-thione-4,5-dithiolate (DMIT), journal=Synthesis, year=1995, volume=1995, issue=3, pages=215–235, doi=10.1055/s-1995-3910 Heating solutions of Na2dmit gives the isomeric 1,2-dithioledithiolate.
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