Trichloroisocyanuric acid in 98% sulfuric acid: A superelectrophilic medium for chlorination of deactivated arenes

Applied Catalysis A: General

Volumn 401, Issue 1-2, 2011, Pages 176-181

  Mendoņa, Gabriela Fonseca ^a   Senra, Mônica Rufino ^a   Esteves, Pierre M ^a   De Mattos, Marcio C S ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Arenes; Aromatic chlorination; DFT Calculations; Superelectrophilic species; Trichloroisocyanuric acid

Indexed keywords

ARENES; AROMATIC CHLORINATION; DFT CALCULATIONS; SUPERELECTROPHILIC SPECIES; TRICHLOROISOCYANURIC ACID;

AROMATIC COMPOUNDS; CHLORINATION;

SULFURIC ACID;

EID: 79959705710     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2011.05.017     Document Type: Article

References (47)

1. G.A. Olah Angew. Chem. Int. Ed. Engl. 32 1993 767 788
2. D.A. Klumpp, Y. Zhang, D. Do, and R. Kartika Appl. Catal. A: Gen. 336 2008 128 132
3. G.A. Olah, and D.A. Klumpp Acc. Chem. Res. 37 2004 211 220
4. S.D.F. Tozetti, L.S. de Almeida, P.M. Esteves, and M.C.S. de Mattos J. Braz. Chem. Soc. 18 2007 675 677
5. G.A. Hiegel, and K.B. Peyton Synth. Commun. 15 1985 385 392
6. G.F. Mendona, H.C. Sindra, L.S. de Almeida, P.M. Esteves, and M.C.S. de Mattos Tetrahedron Lett. 50 2009 473 475
7. G.F. Mendona, A.M. Sanseverino, and M.C.S. de Mattos Synthesis 2003 45 48
8. G.A. Hiegel, C.D. Bayne, and B. Ridley Synth. Commun. 33 2003 1997 2002
9. R.C. Rodrigues, I.M.A. Barros, and E.L.S. Lima Tetrahedron Lett. 46 2005 5945 5947
10. H. Veisi Synthesis 2010 2631 2635
11. M. Wengert, A.M. Sanseverino, and M.C.S. de Mattos J. Braz. Chem. Soc. 13 2002 700 703
12. L. de Luca, and G. Giacomelli Synlett 2004 2180 2184
13. L. de Luca, G. Giacomelli, and G. Nieddu Synlett 2005 223 226
14. A. Shiri, and A. Khoramabadi-Zad Synthesis 2009 2801 2979
15. D.C. Whitehead, R.J. Staples, and B. Borhan Tetrahedron Lett. 50 2009 565 568
16. L.T.C. Crespo, R.S. Ribeiro, M.C.S. de Mattos, and P.M. Esteves Synthesis 2010 2379 2382
17. U. Tilstam, and H. Weinmann Org. Proc. Res. Dev. 6 2002 384 393
18. Z.D. Crane, P.J. Nichols, T. Sammakia, and P.J. Stengel J. Org. Chem. 76 2011 277 280
19. F.A. Carey, and R.J. Sundberg Advanced Organic Chemistry Part B: Reactions and Synthesis 5th ed. 2007 Springer New York pp. 1008-1014
20. G.F. Mendona, and M.C.S. de Mattos Quim. Nova 31 2008 798 801
21. A. Hubbard, T. Okazaki, and K.K. Laali Austr. J. Chem. 60 2007 923 927
22. R.-Y. Tang, P. Zhong, and Q.-L. Lin J. Fluor. Chem. 128 2007 636 640
23. G.K.S. Prakash, T. Mathew, D. Hoole, P.M. Esteves, Q. Wang, G. Rasul, and G.A. Olah J. Am. Chem. Soc. 126 2004 15770 15776
24. P. Bovonsombat, R. Ali, C. Khan, J. Leykajarakul, K. Pla-On, S. Aphimanchindakul, N. Pungcharoenpong, N. Timsuea, A. Arunrat, and N. Punpongjareorn Tetrahedron 66 2010 6928 6935
25. L.S. de Almeida, P.M. Esteves, and M.C.S. de Mattos Synthesis 2006 221 223
26. L.S. de Almeida, P.M. Esteves, and M.C.S. de Mattos Synlett 2006 1515 1518
27. L.S. de Almeida, P.M. Esteves, and M.C.S. de Mattos Synlett 2007 1687 1690
28. R.S. Ribeiro, P.M. Esteves, and M.C.S. de Mattos Synthesis 2011 739 744
29. R.S. Ribeiro, P.M. Esteves, and M.C.S. de Mattos Tetrahedron Lett. 48 2007 8747 8751
30. R.S. Ribeiro, P.M. Esteves, and M.C.S. de Mattos J. Braz. Chem. Soc. 19 2008 1239 1243
31. S.P.L. de Souza, J.F.M. da Silva, and M.C.S. de Mattos J. Braz. Chem. Soc. 14 2003 832 835
32. S.P.L. de Souza, J.F.M. da Silva, and M.C.S. de Mattos Quim. Nova 29 2006 1061 1064
33. M.C.S. de Mattos, and R.B. Bernini Heterocycl. Commun. 12 2006 411 414
34. R. Fletcher Practical Methods of Optimization 1980 Wiley New York
35. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford, CT, 2003.
36. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
37. A.D. Becke J. Chem. Phys. 98 1993 1372 1377
38. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
39. B.S. Moon, H.Y. Choi, H.Y. Koh, and D.Y. Chi Bull. Korean Chem. Soc. 32 2011 472 476
40. H.A. Muathen Tetrahedron 52 1996 8863 8866
41. V.P. Kashparova, E.S. Kagan, I.Y. Zhukova, and E.P. Ivakhnenko Russ. J. Appl. Chem. 77 2004 964 967
42. B.S. Bhatkhande, M.V. Adhikari, and S.D. Samant Ultrason. Sonochem. 9 2002 31 35
43. H.A. Muathen Helv. Chim. Acta 86 2003 164 168
44. M.C. Davis Synth. Commun. 39 2009 1100 1108
45. B.T. Bagmanov Russ. J. Appl. Chem. 82 2009 1570 1576
46. G.F. Mendona, R.R. Magalhães, M.C.S. de Mattos, and P.M. Esteves J. Braz. Chem. Soc. 16 2005 695 698
47. L.S. de Almeida, P.M. Esteves, and M.C.S. de Mattos Tetrahedron Lett. 50 2009 3001 3004