1,2-Ethanedithiol, also known as HSCH2CH2SH, is a chemical compound with a molecular formula of C2H6S2 and a molecular weight of 94.20. It is a commercially available reagent with a boiling point of 146°C and a density of 1.123 g/cm3 at 23°C. It is slightly soluble in water and easily miscible with organic solvents.
When 1,2-Ethanedithiol reacts with aldehydes, ketones, and acetaldehyde, it undergoes condensation reactions to form 1,3-dithiacyclopentane, which is used for carbonyl protection. It exhibits similar stability, condensation selectivity, and carbonyl regeneration conditions as 1,3-propanedithiol. It can be used to protect esters and lactones with enone dithioacetals and/or dithiolactone.
1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons, Inc: New York, 1999. p 201.
2. (a) Oida, T.; Tanimoto, S.; Terao, H.; Okano, M. J. Chem.Soc., Perkin Trans, 1986, 1715. (b) An exception; Barton, D.H. R.; Bielska, M. T.; Cardoso, J. M.; Cussans, N. J.; Ley, S.V. J. Chem. Soc. Perkin Trans I, 1981, 1840.
3. Liu, H. J.; Yeh, W. L.; Chew, S. Y. Tetrahedron Lett., 1993,34, 4435.
4. (a) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem., 1993, 58,4971. (b) Ni, Z. J.; Luh. T. Y. Org. Syn., 1992, 70, 240. (c)Bellesia, F.; Boni, M.; Ghelfi, F.; Pagnoni, U. M. Tetrahedron,1993, 49, 199.
5. (a) Sondej, S. C.; Katzenellenbogen, J. A. J. Org. Chem., 1986,51, 3508. (b) Jeko, J.; Timar, T.; Jaszberenyi, J. C. J. Org.Chem., 1991, 56, 6748.
6. Houghton, R. P.; Dunlop, J. E. Synth. Comun., 1990, 20, 1.
7. Manabe, K.; Iimura, S.; Sun, X. M.; Kobayashi, S. J.Am.Chem. Soc., 2002, 124, 11971.
8. Firouzabadi, H.; Iranpoor, N.; Hazarkhani, H. J. Org. Chem.,2001, 66, 7527.