4,4-Dibromo-3-methylpyrazol-5-one: New applications for selective monobromination of phenols and oxidation of sulfides to sulfoxides

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4865-4868

  Mashraqui, Sabir H ^a   Mudaliar, Chandrashekar D ^a   Hariharasubrahmanian, Harini ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUP; PHENOL DERIVATIVE; SULFIDE; SULFOXIDE;

ARTICLE; BROMINATION; CHEMICAL BOND; CHEMICAL MODIFICATION; OXIDATION; REACTION ANALYSIS;

EID: 0030925264     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01014-9     Document Type: Article

References (29)

1. de la Mare, P. D. Electrophilic Halogenation Cambridge (London) 1976.; Hudlicky, M. Org.Prep.Proced.Int. 1978,10,181.
2. de la Mare, P. D. Electrophilic Halogenation Cambridge (London) 1976.; Hudlicky, M. Org.Prep.Proced.Int. 1978,10,181.
3. Wilson, C.V. Organic Reactions, 1959,9,332-389; Doyle, M.P.; Seigfried, B.; Dellaria Jr, J.F. J.Org.Chem. 1977,42, 2426; McKillop, A.; Bromley, D.; Taylor, E.C. J.Org.Chem.1972,37,88; Barton, D.H.R.; Lacher, B.; Zard, S.Z. Tetrahedron Lett. 1985,26,5939; Bennetau, B.; Krempp, M.; Dunogues, J.; Ratton, S. Tetrahedron Lett. 1992,43,6179; Meyer, A.I.; Fleming, M.P. J.Org.Chem. 1979,44,3405.
4. Wilson, C.V. Organic Reactions, 1959,9,332-389; Doyle, M.P.; Seigfried, B.; Dellaria Jr, J.F. J.Org.Chem. 1977,42, 2426; McKillop, A.; Bromley, D.; Taylor, E.C. J.Org.Chem.1972,37,88; Barton, D.H.R.; Lacher, B.; Zard, S.Z. Tetrahedron Lett. 1985,26,5939; Bennetau, B.; Krempp, M.; Dunogues, J.; Ratton, S. Tetrahedron Lett. 1992,43,6179; Meyer, A.I.; Fleming, M.P. J.Org.Chem. 1979,44,3405.
5. Wilson, C.V. Organic Reactions, 1959,9,332-389; Doyle, M.P.; Seigfried, B.; Dellaria Jr, J.F. J.Org.Chem. 1977,42, 2426; McKillop, A.; Bromley, D.; Taylor, E.C. J.Org.Chem.1972,37,88; Barton, D.H.R.; Lacher, B.; Zard, S.Z. Tetrahedron Lett. 1985,26,5939; Bennetau, B.; Krempp, M.; Dunogues, J.; Ratton, S. Tetrahedron Lett. 1992,43,6179; Meyer, A.I.; Fleming, M.P. J.Org.Chem. 1979,44,3405.
6. Wilson, C.V. Organic Reactions, 1959,9,332-389; Doyle, M.P.; Seigfried, B.; Dellaria Jr, J.F. J.Org.Chem. 1977,42, 2426; McKillop, A.; Bromley, D.; Taylor, E.C. J.Org.Chem.1972,37,88; Barton, D.H.R.; Lacher, B.; Zard, S.Z. Tetrahedron Lett. 1985,26,5939; Bennetau, B.; Krempp, M.; Dunogues, J.; Ratton, S. Tetrahedron Lett. 1992,43,6179; Meyer, A.I.; Fleming, M.P. J.Org.Chem. 1979,44,3405.
7. Wilson, C.V. Organic Reactions, 1959,9,332-389; Doyle, M.P.; Seigfried, B.; Dellaria Jr, J.F. J.Org.Chem. 1977,42, 2426; McKillop, A.; Bromley, D.; Taylor, E.C. J.Org.Chem.1972,37,88; Barton, D.H.R.; Lacher, B.; Zard, S.Z. Tetrahedron Lett. 1985,26,5939; Bennetau, B.; Krempp, M.; Dunogues, J.; Ratton, S. Tetrahedron Lett. 1992,43,6179; Meyer, A.I.; Fleming, M.P. J.Org.Chem. 1979,44,3405.
8. Wilson, C.V. Organic Reactions, 1959,9,332-389; Doyle, M.P.; Seigfried, B.; Dellaria Jr, J.F. J.Org.Chem. 1977,42, 2426; McKillop, A.; Bromley, D.; Taylor, E.C. J.Org.Chem.1972,37,88; Barton, D.H.R.; Lacher, B.; Zard, S.Z. Tetrahedron Lett. 1985,26,5939; Bennetau, B.; Krempp, M.; Dunogues, J.; Ratton, S. Tetrahedron Lett. 1992,43,6179; Meyer, A.I.; Fleming, M.P. J.Org.Chem. 1979,44,3405.
9. a) Tokiyama, H.; Hirakawa, T.; Okamoto, T. Chem.Lett. 1987,627
10. b) Keith, S.; Martin, J.D.; Ian, M.; Martin, R.B. J.Chem.Soc. Perkin Trans.I. 1992,15,1877
11. c) Muathen, H.A. J.Org.Chem. 1992,57,2740
12. d) Calo, V.; Ciminale, F.; Lopez, L.; Todesco, P.E. J.Chem.Soc.C,1971,3652
13. e) Guy, A.; Lemaire, M.; Guette, J.P. Tetrahedron, 1982, 38, 2347
14. f) Fuchs, B.; Belsky, Y.; Tartakovsky, J.; Zizhuashvili.; Weinmann, S. J.Chem.Soc.Chem.Commun.1982,778
15. g) Mitchell, R.H.; Lai, Y.H.; William, R.V. J.Org.Chem.1979,25,4733.
16. a) Vogel, A.I. Textbook of Practical Organic Chemistry, 5th ed. Longman (London) 1989, pp. 807-8
17. b) Carpino, L.A.; Terry, P.H.; Thatte, S.D. J.Org.Chem. 1966,31,2867
18. c) Kosower, E.M.; Faust, D.; Ben-Shoshan, B.; Goldberg, I. J.Org.Chem. 1982,47,214.
19. d) Caprino, L.A. J.Am.Chem.Soc. 1958,80,599.
20. Ingold, C.K. Stucture and Mechanism in Organic Chemistry,2nd ed. Cornell Univ.Press.Ithaca(NY) 1969.
21. Madesclaire, M. Tetrahedron 1986,42,5459 and references cited therein; Drabowicz, J.; Lyzwa, P. Synthesis, 1990,937; Roh, R.R.; Kim, K.S.; Kim, Y.H. Tetrahedron Lett. 1991,32,799; Firouzabadi, H.; Mohammadpour-Baltrok, I. Bull.Chem.Soc.Jpn. 1992,65,1131, McKillop, A.; Tarbin, J.A. Tetrahedron Lett. 1983,1505; Ley, S.V.; Williams, D.J. J.Chem.Soc.Chem.Commun. 1990,1219; Hirano, M.; Kudo, H.; Morimoto, T. Bull. Chem.Soc.Jpn. 1994,67,1492.
22. Madesclaire, M. Tetrahedron 1986,42,5459 and references cited therein; Drabowicz, J.; Lyzwa, P. Synthesis, 1990,937; Roh, R.R.; Kim, K.S.; Kim, Y.H. Tetrahedron Lett. 1991,32,799; Firouzabadi, H.; Mohammadpour-Baltrok, I. Bull.Chem.Soc.Jpn. 1992,65,1131, McKillop, A.; Tarbin, J.A. Tetrahedron Lett. 1983,1505; Ley, S.V.; Williams, D.J. J.Chem.Soc.Chem.Commun. 1990,1219; Hirano, M.; Kudo, H.; Morimoto, T. Bull. Chem.Soc.Jpn. 1994,67,1492.
23. Madesclaire, M. Tetrahedron 1986,42,5459 and references cited therein; Drabowicz, J.; Lyzwa, P. Synthesis, 1990,937; Roh, R.R.; Kim, K.S.; Kim, Y.H. Tetrahedron Lett. 1991,32,799; Firouzabadi, H.; Mohammadpour-Baltrok, I. Bull.Chem.Soc.Jpn. 1992,65,1131, McKillop, A.; Tarbin, J.A. Tetrahedron Lett. 1983,1505; Ley, S.V.; Williams, D.J. J.Chem.Soc.Chem.Commun. 1990,1219; Hirano, M.; Kudo, H.; Morimoto, T. Bull. Chem.Soc.Jpn. 1994,67,1492.
24. Madesclaire, M. Tetrahedron 1986,42,5459 and references cited therein; Drabowicz, J.; Lyzwa, P. Synthesis, 1990,937; Roh, R.R.; Kim, K.S.; Kim, Y.H. Tetrahedron Lett. 1991,32,799; Firouzabadi, H.; Mohammadpour-Baltrok, I. Bull.Chem.Soc.Jpn. 1992,65,1131, McKillop, A.; Tarbin, J.A. Tetrahedron Lett. 1983,1505; Ley, S.V.; Williams, D.J. J.Chem.Soc.Chem.Commun. 1990,1219; Hirano, M.; Kudo, H.; Morimoto, T. Bull. Chem.Soc.Jpn. 1994,67,1492.
25. Madesclaire, M. Tetrahedron 1986,42,5459 and references cited therein; Drabowicz, J.; Lyzwa, P. Synthesis, 1990,937; Roh, R.R.; Kim, K.S.; Kim, Y.H. Tetrahedron Lett. 1991,32,799; Firouzabadi, H.; Mohammadpour-Baltrok, I. Bull.Chem.Soc.Jpn. 1992,65,1131, McKillop, A.; Tarbin, J.A. Tetrahedron Lett. 1983,1505; Ley, S.V.; Williams, D.J. J.Chem.Soc.Chem.Commun. 1990,1219; Hirano, M.; Kudo, H.; Morimoto, T. Bull. Chem.Soc.Jpn. 1994,67,1492.
26. Madesclaire, M. Tetrahedron 1986,42,5459 and references cited therein; Drabowicz, J.; Lyzwa, P. Synthesis, 1990,937; Roh, R.R.; Kim, K.S.; Kim, Y.H. Tetrahedron Lett. 1991,32,799; Firouzabadi, H.; Mohammadpour-Baltrok, I. Bull.Chem.Soc.Jpn. 1992,65,1131, McKillop, A.; Tarbin, J.A. Tetrahedron Lett. 1983,1505; Ley, S.V.; Williams, D.J. J.Chem.Soc.Chem.Commun. 1990,1219; Hirano, M.; Kudo, H.; Morimoto, T. Bull. Chem.Soc.Jpn. 1994,67,1492.
27. Madesclaire, M. Tetrahedron 1986,42,5459 and references cited therein; Drabowicz, J.; Lyzwa, P. Synthesis, 1990,937; Roh, R.R.; Kim, K.S.; Kim, Y.H. Tetrahedron Lett. 1991,32,799; Firouzabadi, H.; Mohammadpour-Baltrok, I. Bull.Chem.Soc.Jpn. 1992,65,1131, McKillop, A.; Tarbin, J.A. Tetrahedron Lett. 1983,1505; Ley, S.V.; Williams, D.J. J.Chem.Soc.Chem.Commun. 1990,1219; Hirano, M.; Kudo, H.; Morimoto, T. Bull. Chem.Soc.Jpn. 1994,67,1492.
28. Hazlet, S.E. J.Am.Chem.Soc. 1940,62,2159.
29. Tagaki, W.; Kiso, S.; Oae, S. Bull.Chem.Soc.Jpn. 1965,38,414.