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Activated Zeolites and Heteropolyacids: An Efficient Catalysts for the Synthesis of Triacetoxyaromatic Precursors of Hydroxyquinones
Corresponding Author(s) : Dokari Hadjila
Asian Journal of Chemistry,
Vol. 25 No. 11 (2013): Vol 25 Issue 11
Abstract
The Thiele-Winter reaction is of interest for synthesis of triacetoxyaromatic precursors of hydroquinones. Liquid acid such as, chlorosulfonic acid and solid acids like heteropolyacids have an efficient catalyst can effectively replace sulfuric acid in acetoxylation reaction of quinones without use of organic solvent at room temperature.
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- J.F.W. McOmie and J.M. Blatchey, Org. React., 19, 199 (1972).
- S. Spyroudis, Molecules, 5, 1291 (2000).
- A.M. Lira, A.A.S. Araújo, I.D.J. Basílio, B.L.L. Santos, D.P. Santana and R.O. Macedo, Thermochim. Acta, 457, 1 (2007).
- R. Sauriasari and K. Ogino, Toxicology, 235, 103 (2007); in ed.: M. Windholz, The Merck Index; Merck and Co, Rahway, USA, edn. 12 (1993).
- A. Combes, Bull. Soc. Chim., 1, 800 (1907); C.J. Soderquist, J. Chem., 50, 782 (1973).
- J.J. Kessl and N.V. Moskalev, Biochim. Biophys. Acta, 1767, 319 (2007).
- M.B. Teimouri and H.R. Khavasi, Tetrahedron, 63, 10269 (2007); C. Valente, Med. Bioorg., 15, 5340 (2007).
- J. Thiele, Ber., 31, 1247 (1898).
- J. Thiele and E. Winter, Ann., 311, 341 (1900).
- H. Burton and P.F.G. Praill, J. Chem. Soc., 755 (1952).
- R.J. Gillepsi, Can. Chem. Educ., 4, 9 (1969).
- Aldrich-Chemie, France (1995).
- M. Windholz, éd., The Merck Index; Merck and Co, Rahway, USA, edn 12 (1993).
- J.K. Muchie and J.A. Miller, Synthesis, 824 (1981).
- K.S. Kochlar, B.S. Bal and R.P. Deshpande, J. Org. Chem., 48, 1785 (1983).
- K.J. Elbs, Prakt. Chem., 48, 179 (1993).
- D. Villemin and M. Hammadi, Actes of 3th Colloque Franco-Magrébin; 611 (1996).
- N.F. Hull and J.B. Conant, J. Am. Chem. Soc., 49, 3047 (1927): G.A. Olah, G.K.S. Pradash and J. Sommer, Superacids, Wiley, New York (1985); G.A. Olah, Angew. Chem. Int. Ed. Engl., 32, 727 (1993); D. Villemin and M. Richard, React. Kinet. Catal. Lett., 52, 355 (1994).
- Y. Izumi, K. Urabe and M. Onaka, in: Zeolite, Clay and Heteropolyacid, in Organic Reactions, Tokyo-kodansha-Weinheim, VCHI, pp. 100-120 (1992); P. Dupont and F. Lefebvre, J. Mol. Catal. A, 114, 299 (1996).
- Y. Izumi and K. Matsuo, J. Mol. Catal., 18, 299 (1983).
References
J.F.W. McOmie and J.M. Blatchey, Org. React., 19, 199 (1972).
S. Spyroudis, Molecules, 5, 1291 (2000).
A.M. Lira, A.A.S. Araújo, I.D.J. Basílio, B.L.L. Santos, D.P. Santana and R.O. Macedo, Thermochim. Acta, 457, 1 (2007).
R. Sauriasari and K. Ogino, Toxicology, 235, 103 (2007); in ed.: M. Windholz, The Merck Index; Merck and Co, Rahway, USA, edn. 12 (1993).
A. Combes, Bull. Soc. Chim., 1, 800 (1907); C.J. Soderquist, J. Chem., 50, 782 (1973).
J.J. Kessl and N.V. Moskalev, Biochim. Biophys. Acta, 1767, 319 (2007).
M.B. Teimouri and H.R. Khavasi, Tetrahedron, 63, 10269 (2007); C. Valente, Med. Bioorg., 15, 5340 (2007).
J. Thiele, Ber., 31, 1247 (1898).
J. Thiele and E. Winter, Ann., 311, 341 (1900).
H. Burton and P.F.G. Praill, J. Chem. Soc., 755 (1952).
R.J. Gillepsi, Can. Chem. Educ., 4, 9 (1969).
Aldrich-Chemie, France (1995).
M. Windholz, éd., The Merck Index; Merck and Co, Rahway, USA, edn 12 (1993).
J.K. Muchie and J.A. Miller, Synthesis, 824 (1981).
K.S. Kochlar, B.S. Bal and R.P. Deshpande, J. Org. Chem., 48, 1785 (1983).
K.J. Elbs, Prakt. Chem., 48, 179 (1993).
D. Villemin and M. Hammadi, Actes of 3th Colloque Franco-Magrébin; 611 (1996).
N.F. Hull and J.B. Conant, J. Am. Chem. Soc., 49, 3047 (1927): G.A. Olah, G.K.S. Pradash and J. Sommer, Superacids, Wiley, New York (1985); G.A. Olah, Angew. Chem. Int. Ed. Engl., 32, 727 (1993); D. Villemin and M. Richard, React. Kinet. Catal. Lett., 52, 355 (1994).
Y. Izumi, K. Urabe and M. Onaka, in: Zeolite, Clay and Heteropolyacid, in Organic Reactions, Tokyo-kodansha-Weinheim, VCHI, pp. 100-120 (1992); P. Dupont and F. Lefebvre, J. Mol. Catal. A, 114, 299 (1996).
Y. Izumi and K. Matsuo, J. Mol. Catal., 18, 299 (1983).