Efficient halogenation of aromatic systems using N-halosuccinimides in ionic liquids

Advanced Synthesis and Catalysis

Volumn 346, Issue 1, 2004, Pages 77-82

  Yadav, J S ^a   Reddy, B V S ^a   Reddy, P S R ^a   Basak, A K ^a   Narsaiah, A V ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Arenes; Electrophilic halogenation; Haloarenes; Ionic liquids (ILs)

Indexed keywords

AROMATIC COMPOUND; ION; SUCCINIMIDE DERIVATIVE;

ARTICLE; BROMINATION; HALOGENATION; INFRARED SPECTROSCOPY; LIQUID; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTITATIVE ANALYSIS; REDUCTION; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 1642445603     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303229     Document Type: Article

References (30)

1. C. Christophersen, Acta Chem. Scand. B 1985, 39, 515.
2. a) P. B. De la Mare, Electrophilic Halogenation, Cambridge University Press, Cambridge, 1976, Chapter 5;
3. b) S. Torii, H. Tanaka, T. Siroi, M. Akada, J. Org. Chem. 1979, 44, 3305;
4. c) C. E. Coburn, D. K. Anderson, J. S. Swenton, J. Org. Chem. 1983, 48, 1455.
5. a) G. Majetich, R. Hicks, S. Reister, J. Org. Chem. 1997, 62, 4321;
6. b) S. C. Roy, C. Guin, K. K. Rana, G. Maiti, Tetrahedron Lett. 2001, 42, 6941;
7. c) L. A. Yanovskaya, A. P. Terentyev, L. I. Belenky, J. Gen. Chem. USSR (Engl. Transl.) 1952, 22, 1635.
8. a) K. W. Rosenmund, W. Kuhnhenn, Ber. Dtsch. Chem. Ges. 1923, 56, 1262;
9. b) H. A. Muathen, J. Org. Chem. 1992, 57, 2740;
10. c) S. Kajigaeshi, T. Kakinami, T. Okamoto, H. Nakamura, M. Fujikawa, Bull. Chem. Soc. Jpn. 1987, 60, 4187;
11. d) D. J. Cram, I. B. Dicker, M. Lauer, C. B. Knobler, K. N. Trueblood, J. Am. Chem. Soc. 1984, 106, 7150.
12. a) N. P. Buu-Hou, Justus Liebigs Ann. Chem. 1944, 556, 1-9;
13. b) J. C. Roberts, P. Roffey, J. Chem. Soc. (C) 1966, 160.
14. a) G.-J. M. Gruter, O. S. Akkerman, F. Bickelhaupt, J. Org. Chem. 1994, 59, 4473;
15. b) Y. Goldberg, C. Bensimon, H. Alper, J. Org. Chem. 1992, 57, 6374.
16. a) G. A. Olah, Q. Wang, G. Sandford, G. K. S. Prakash, J. Org. Chem. 1993, 58, 3194;
17. b) T. Oberhauser, J. Org. Chem. 1997, 62, 4504;
18. c) R. S. Coleman, E. B. Grant, J. Org. Chem. 1991, 56, 1357;
19. d) V. Paul, A. Sudalai, T. Daniel, K. V. Srinivasan, Tetrahedron Lett. 1994, 35, 7055.
20. a) M. C. Carreno, J. L. Garcia Ruano, G. Sanz, M. A. Toledo, A. Urbano, J. Org. Chem. 1995, 60, 5328;
21. b) R. H. Mitchel, Y. H. Lai, R. V. Williams, J. Org. Chem. 1979, 44, 4733;
22. c) S. D. Ross, M. Finkelstein, R. C. Petersen, J. Am. Chem. Soc. 1958, 80, 4327.
23. a) T. Welton, Chem. Rev. 1999, 99, 2071;
24. b) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772.
25. R. Sheldon, Chem. Commun. 2001, 2399.
26. R. Rajagopal, D. V. Jarikote, R. J. Lahoti, T. Daniel, K. V. Srinivasan, Tetrahedron Lett. 2003, 44, 1815.
27. a) F. L. Lambert, W. D. Ellis, R. J. Parry, J. Org. Chem. 1965, 30, 304;
28. b) W. J. Bailey, J. Bello, J. Org. Chem., 1955, 20, 525.
29. a) T. Oberhauser, J. Org. Chem. 1997, 62, 4504;
30. b) M. C. Carreno, J. L. Garcia Ruano, G. Sanz, M. A. Toledo, A. Urbano, Tetrahedron Lett. 1996, 37, 4081.