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Ethane-1,2-dithiol
Chemical compound C2H4(SH)2 From Wikipedia, the free encyclopedia
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Ethane-1,2-dithiol, also known as EDT,[1] is a colorless liquid with the formula C2H4(SH)2. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions.
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Preparation
Ethane-1,2-dithiol is made commercially by the reaction of 1,2-dichloroethane with aqueous sodium bisulfide. In the laboratory, it can also be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis.[2]
Reactions
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1,2-Ethanedithiol is a weak acid, typical of alkyl thiols. In the presence of base and an alkylating agent, 1,2-ethanedithiol converts to thioethers:
- HS(CH2)2SH + 2 NR3 + 2 R'I → R'S(CH2)2SR' + 2 [R3NH]I
Oxidation of 1,2-ethanedithiol gives a series of oligomers, including the cyclic bis(disulfide).[3]
As a 1,2-dithiol, this compound reacts with aldehydes and ketones to give 1,3-dithiolanes, which can be useful intermediates.[4]
Other 1,2- and 1,3-dithiols give related 1,3-dithiolanes (five-membered) and 1,3-dithianes (six-membered rings). Diols such as ethylene glycol undergo analogous reactions to give 1,3-dioxolanes. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated.
1,2-Ethanedithiol has been used as a scavenger in peptide cleavage synthesis.[citation needed]
Like 1,3-propanedithiol, 1,2-ethanedithiol readily forms metal thiolate complexes. Illustrative is the synthesis of the derivative diiron ethanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl:[5]
- Fe3(CO)12 + C2H4(SH)2 → Fe2(S2C2H4)(CO)6 + H2 + Fe(CO)5 + CO
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See also
References
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