1,2-Ethanedithiol
1,2-Ethanedithiol is an odorous, colorless liquid with the formula C2H4(SH)2. It is a common building block in organic synthesis and an excellent ligand for metal ions.
Applications in organic chemistry
It is widely used in organic chemistry because it reacts with aldehydes and ketones to give 1,3-dithiolanes, which are useful intermediates. [1]
-
- C2H4(SH)2 + RR'CO → C2H4S2CRR' + H2O
Other 1,2- and 1,3-dithiols undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings). Diols such as ethylene glycol undergo analogous reactions to 1,3-dioxalanes and 1,3-dioxanes. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated.
Synthesis
It can be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis.[2]
References
- ^ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
- ^ Speziale, A. J. (1963). "Ethanedithiol". Org. Synth.; Coll. Vol. 4: 401.
|
Top