A combined experimental and theoretical investigation on the oxygenation of organic sulfides by oxo(salen)chromium(V) ion

Journal of Physical Organic Chemistry

Volumn 22, Issue 7, 2009, Pages 650-660

  Venkataramanan, Natarajan Sathiyamoothy ^a,b   Rajagopal, Seenivasan ^b   Suvitha, Ambigapathy ^a   Kawazoe, Yoshiyuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

DFT; Mechanism; Oxidation; Salen; Sulfoxides

Indexed keywords

CR ATOMS; DENSITY FUNCTIONAL THEORY METHODS; DFT; DONOR LIGANDS; ELECTRON-RICH; FIRST ORDER; FREE ENERGY CHANGE; HAMMETT PLOTS; HARMONIC FREQUENCY; LOW-ACTIVATION ENERGY; NEGATIVE CHARGE; ORGANIC SULFIDES; P-VALUE; POSITIVE CHARGES; PRODUCT YIELDS; SALEN; SPECTRAL STUDIES; SPIN DENSITIES; SPIN STATE; SULFOXIDES; SULFUR ATOMS; THEORETICAL INVESTIGATIONS; THERMODYNAMIC ENERGY; TRANSITION STATE; TWO-ELECTRON TRANSFER;

ACTIVATION ENERGY; ATOMS; CHROMIUM; DENSITY FUNCTIONAL THEORY; DIMETHYL SULFOXIDE; FREE RADICAL REACTIONS; LIGANDS; OXIDANTS; OXIDATION; OXYGENATION; OXYGENATORS; PROBABILITY DENSITY FUNCTION; REACTION RATES; SPECTROSCOPIC ANALYSIS; SPIN DYNAMICS; SUBSTRATES; SULFUR;

CHROMIUM COMPOUNDS;

EID: 67650845119     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1496     Document Type: Article

References (82)

1. M. C. Carreno, Chem. Rev. 1995, 95, 1717-1760.
2. I. Fernandez, N. Khiar, Chem. Rev. 2003, 103, 3651-3705.
3. R. Bentley, Chem. Soc. Rev. 2005, 34, 609-624.
4. B. Meunier (Ed.), Biomimetic Oxidations Catalyzed by Transition Metal Complexes, Imperial College Press, London, 2000.
5. F. Montarari, L. Casella (Eds), Metalloporphyrins Catalysed Oxidation, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1994.
6. F. A. Cotton, J. Chem. Soc., Dalton Trans. 2000, 1961-1968.
7. R. H. Holm, Chem. Rev. 1987, 87, 1401-1449.
8. L. Alessandra, A. Scettri, J. Organomet. Chem. 2006, 691, 2072-2082.
9. W. R. Thiel, Coord. Chem. Rev. 2003, 245, 95-106.
10. E. M. McGarrigle, D. G. Gilheany, Chem. Rev. 2005, 105, 1563-1602.
11. N. S. Venkataramanan, K. Gobi, S. Rajagopal, Coord. Chem. Rev. 2005,249, 1249-1268.
12. K. P. Bryliakov, E. P. Talsi, Curr. Org. Chem. 2008, 12, 386-404.
13. K. C. Gupta, A. K. Sutar, Coord. Chem. Rev. 2008, 252, 1420-1450.
14. P. G. Cozzi, Chem. Soc. Rev. 2004, 33, 410-421.
15. T. Uchida, R. Irie, T. Katsuki, J. Synth. Org. Chem. Jpn. 2005, 63, 478-491.
16. K. M. Ryan, C. Bousquent, D. G. Gilheany, Tetrahedron Lett. 1999, 40,3613-3616.
17. A. M. Daly, C. T. Dalton, M. F. Renehan, D. G. Gilheany, Tetrahedron Lett.1999, 40, 3617-3620.
18. C. T. Dalton, K. M. Ryan, V. M. Wall, C. Bousquet, D. G. Gilheany, Top. Catal. 1998, 5, 75-91.
19. A. M. Daly, M. F. Renehan, D. G. Gilheany, Org. Lett. 2001, 3, 663-666.
20. C. P. O'Mahony, E. M. McGarrigle, M. F. Renehan, K. M. Ryan, N. J.Kerrigan, C. Bousquent, D. G. Gilheany, Org. Lett. 2001, 3, 3435-3438.
21. D. M. Daly, D. G. Gilheany, Tetrahedron:Asymmetry 2003, 14, 127-137.
22. C. T. Dalton, K. M. Ryan, I. J. Langan, E. J. Coyne, D. G. Gilehany, J. Mol.Catal. A Chem. 2002, 187, 179-187.
23. E. M. McGarrigle, D. M. Murphy, D. G. Gilheany, Tetrahedron: Asymmetry 2004, 15, 1343-1354.
24. N. J. Kerrigan, H. Muller-Bunz, D. G. Gilheany, J. Mol. Catal. A 2005,227, 163-172.
25. E. F. Clarke, E. M. McGarrigle, D. G. Gilheany, Arkivoc 2005, 30-38.
26. R. Sevvel, S. Rajagopal, C. Srinivasan, N. M. I. Alhaji, A. Chellamani,J. Org. Chem. 2000, 65, 3334-3340.
27. H. Egami, T. Katsuki, Synlett 2008, 1543-1546.
28. K. Matsumoto, T. Yamaguchi, T. Katsuki, Chem. Commun. 2008, 14, 1704-1706.
29. K. Matsumoto, T. Yamaguchi, J. Fujisaki, B. Saito, T. Katsuki, Chem.Asian J. 2008, 3, 351-358.
30. H. Egami, T. Katsuki, J. Am. Chem. Soc. 2007, 129, 3616-3627.
31. T. Yamaguchi, K. Matsumoto, B. Saito,T. Katsuki, Angew. Chem., Int. Ed.2007, 46, 4729-4731.
32. K. P. Bryliakov, E. P. Talsi, Eur. J. Org. Chem. 2008, 19, 3369-3376.
33. A. L. Nuzhdin,D. N. Dybtsev, K. P. Bryliakov, E. P.Talsi,J.Am. Chem. Soc.2007, 129, 12958-12960.
34. K. P. Bryliakov, E. P. Talsi, Chem. A Eur. J. 2007, 13, 8045-8050.
35. K. P. Bryliakov, E. P. Talsi, J. Mol. Catal. A 2007, 264, 280-287.
36. K. P. Bryliakov, E. P. Talsi, Angew. Chem., Int. Ed. 2004, 43, 5228-5230.
37. J. Legros, C. Bolm, Adv. Synth. Catal. 2005, 347, 19-31.
38. J. Legros, C. Bolm, Angew. Chem., Int. Ed. 2004, 43, 4225-4228.
39. J. Legros, C. Bolm, Angew. Chem., Int. Ed. 2003, 42, 5487-5489.
40. C. Bolm, F. Bienewald, Angew Chem., Int. Ed. 1996, 34, 26402642.
41. S. Velusamy, A. V. Kumar, R. Saini, T. Punniyamurthy, Tetrahedron Lett.2005, 46, 3819-3822.
42. Y. Lee, D. H. Lee, A. A. N. Sarjeant, L. N. Zakharov, A. L. Rheingold, K. D.Karlin, Inorg. Chem. 2006, 45, 10098-10107.
43. F. Hosseinpoor, H. Golchoubian, Tetrahedron Lett. 2006, 47, 5195-5197.
44. E. Samsel, K. Srinivasan, J. K. Kochi, J. Am. Chem. Soc. 1985, 107, 7606-7616.
45. K. Srinivasan, J. K. Kochi, Inorg. Chem. 1985, 24, 4671-4679.
46. P.G. Slade, N. D. Priestley, K. D. Sugden, Org. Lett. 2007, 9, 4411-4414.
47. P. Premsingh, N. S. Venkataramanan, S. Rajagopal, S. P. Mirza, M. Vairamani, P. S. Rao, K. Velavan, Inorg. Chem. 2004, 43, 5744-5753.
48. N. S. Venkataramanan, S. Rajagopal, M. Vairamani, J. Inorg. Biochem.2007, 101 , 274-282.
49. N. S. Venkataramanan, S. Premsingh, S. Rajagopal, K. Pitchumani, J.Org. Chem. 2003, 68, 7460-7470.
50. N. S. Venkataramanan, S. Rajagopal, Tetrahedron 2006, 62,5645-5651.
51. S. S. Kim, G. Rajagopal, Synthesis 2003, 16, 2461-2463.
52. C. R. J. Lepage, L. Mihichuk, D. G. Lee, Can. J. Chem. 2003, 81 , 75-80.
53. J. S. Sears, C. D. Sherrill, J. Chem. Phys. 2006, 124, 144314-144320.
54. H. Jacobsen, L. Cavallo, Organometallics 2006, 25, 177-183.
55. L. Cavallo, H. Jacobsen, Eur. J. Org. Chem. 2003, 5, 892-902.
56. Y. G. Abashkin, J. R. Collins, S. K. Burt, Inorg. Chem. 2001, 40, 4040-4048.
57. Y. G. Abashkin, S. K. Burt, J. Phys. Chem. B 2004, 108, 2708-2711.
58. I. V. Khavrutskii, D. G. Musaev, K. Morokuma, J. Am. Chem. Soc. 2003, 125, 13879-13889.
59. P. Brandt, P. O. Norrby, A. M. Daly, D. G. Gilheany, Chem - Eur. J. 2002, 8, 4299-4307.
60. M. Calligaris, Coord. Chem. Rev. 2004, 248, 351-375.
61. R. Mariz, X. Luan, M. Gatti, A. Linden, R. Dorta, J. Am. Chem. Soc. 2008,130, 2172-2173.
62. S. Roman, V. Mody, A. A. Zareba, M. B. Zaczek, M. Gateuzowski, V.Sashuk, K. Grela, D. T. Gryko, Inorg. Chem. 2007, 46, 5616.
63. M. Madesclaire, Tetrahedron 1986, 42, 5459.
64. H. Saltzman, J. G. Sharefkin, Organic Synthesis, Collect Vol. V, Wiley,New York, NY, 1973, 658.
65. T. L. Siddall, N. Miyura, J. C. Juffman, J. K. Kochi, J. Chem. Soc., Chem.Commun. 1983, 1185-1186.
66. C. Srinivasan, A. Chellamani, S. Rajagopal, J. Org. Chem. 1985, 50, 1201-1205.
67. 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 03, Revision D.01,Gaussian, Inc., Wallingford CT (2004).
68. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
69. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
70. Binding constant for DMSO with xo(salen)chromium(V) complexes are estimated by using Benesi-Hildebrand equation. For details see Supporting Information.
71. V. K. Sivasubramanian, M. Ganesan, S. Rajagopal, R. Ramaraj, J. Org. Chem. 2002, 67, 1506-1514.
72. M. Palucki, N. S. Fenny, P. J. Pospisil, M. L. Guler, T. Ishida, E. N.Jacobsen, J. Am. Chem. Soc. 1998, 120, 948-954.
73. A. Chellamani, P. Kulanthiaipandi, S. Rajagopal, J. Org. Chem. 1999, 64, 2232-2239.
74. K. P. Bryliakov, M. V. Lobanova, E. P. Talsi, J. Chem. Soc., Dalton Trans. 2002, 11, 2263-2265.
75. K. P. Bryliakov, E. P. Talsi, Inorg. Chem. 2003, 42, 7258-7265.
76. J. S. Sears, C. D. Sherrill, J. Phys. Chem. A 2008, 112, 6741-6752.
77. J. S. Sears, C. D. Sherrill, J. Phys. Chem. A 2008, 112, 3466-3477.
78. E. Tkatchouk, L. Fomina, E. Rivera, S. Fomine, J. Mol. Struct. 2005, 729, 147-154.
79. S. Chang, J. M. Galvin, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 6937-6938.
80. N. Hosoya, A. Hatakeyama, K. Yanai, H. Fujii, R. Irie, T. Katasuki, Synlett 1993, 641-645.
81. D. A. House, P. J. Steel, Inorg. Chim. Acta 1998, 269, 229-234.
82. V. Felix, T. M. Santos, J. Madureira, F. Mirante, S. Quintal, B. J. Good- fellow, M. G. S. Marques, J. de Jesus, P. Drew, M. J. Calhorda, Inorg. Chim. Acta 2003, 356, 335-342.