Mechanistic study on the oxidation of (phenylthio)acetic acids by oxo(salen)manganese(V) complexes and the reactivity-selectivity principle

Journal of Molecular Catalysis A: Chemical

Volumn 283, Issue 1-2, 2008, Pages 83-92

  Chellamani, Arunachalam ^a   Sengu, Paramasivan ^a  

^a MANONMANIAM SUNDARANAR UNIVERSITY   (India)

Author keywords

(Phenylthio)acetic acids; (Salen)MnIII complexes; Catalyzed oxidation; Iodosylbenzene; Reaction mechanism

Indexed keywords

ACETIC ACID; CATALYST SELECTIVITY; CATALYTIC OXIDATION; MANGANESE COMPOUNDS; REACTION KINETICS; SUBSTITUTION REACTIONS;

(PHENYLTHIO)ACETIC ACIDS; IODOSYLBENZENE; OXO(SALEN)MANGANESE COMPLEXES;

CARBOXYLIC ACIDS;

EID: 40049083129     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2007.12.004     Document Type: Article

References (69)

1. In: Meunier B. (Ed). Biomimetic Oxidations Catalyzed by Transition Metal Complexes (2000), Imperial College Press, London
2. In: Meunier B. (Ed). Metal-Oxo and Metal-Peroxo Species in Catalytic Oxidations, Structure and Bonding, vol. 97 (2000), Springer, Berlin
3. Srinivasan K., Michaud P., and Kochi J.K. J. Am. Chem. Soc. 108 (1986) 2309
4. Venkataramanan N.S., Kuppuraj G., and Rajagopal S. Coord. Chem. Rev. 249 (2005) 1249
5. Curci R., Giannattasio S., Sciacovelli O., and Troisi L. Tetrahedron 40 (1984) 2763
6. Takata T., Tajima R., and Ando W. Phosphorous Sulfur Silicon 16 (1983) 67
7. Acquaye J.H., Muller J.G., and Takeuchi K.J. Inorg. Chem. 32 (1993) 160
8. Chellamani A., Alhaji N.M.I., Rajagopal S., Sevvel R., and Srinivasan C. Tetrahedron 51 (1995) 12677
9. Chellamani A., and Alhaji N.M.I. Indian J. Chem. 38A (1999) 888
10. Chellamani A., Alhaji N.M.I., and Rajagopal S. J. Chem. Soc., Perkin Trans. 2 (1997) 299 and references cited therein
11. Chellamani A., Kulanthaipandi P., and Rajagopal S. J. Org. Chem. 64 (1999) 2232
12. Sevvel R., Rajagopal S., Srinivasan C., Alhaji N.M.I., and Chellamani A. J. Org. Chem. 65 (2000) 3334
13. Chellamani A., and Harikengaram S. J. Phys. Org. Chem. 16 (2003) 589
14. Chellamani A., and Harikengaram S. J. Chem. Res. (2004) 728
15. Chellamani A., and Harikengaram S. J. Mol. Catal. A 247 (2006) 260
16. Chellamani A., Alhaji N.M.I., and Rajagopal S. J. Phys. Org. Chem. 20 (2007) 255
17. Venkataramanan N.S., Premsingh S., Rajagopal S., and Pitchumani K. J. Org. Chem. 68 (2003) 7460
18. Sivasubramanian V.K., Ganesan M., Rajagopal S., and Ramaraj R. J. Org. Chem. 67 (2002) 1506
19. Gelb M.H., Toscano Jr. W.A., and Sligar S.C. Proc. Natl. Acad. Sci. U.S.A. 79 (1982) 5758
20. Pecoraro V.L. Photochem. Photobiol. 48 (1988) 249
21. In: Sheldon R.A. (Ed). Metalloporphyrins in Catalytic Oxidations (1994), Marcel Dekker, New York
22. Palucki M., Finney N.S., Pospisil P.J., Güler M.L., Ishida T., and Jacobsen E.N. J. Am. Chem. Soc. 120 (1998) 948
23. Ludwig M., Pattridge K.A., and Stallings W.C. Manganese in Metabolism and Enzyme Function (1986), Academic Press, New York p. 405 (Chapter 21)
24. Silvarman J., and Dodson R.W. J. Phys. Chem. 56 (1952) 846
25. Srinivasan C., Kuthalingam P., and Arumugam N. J. Chem. Soc., Perkin Trans. 2 (1980) 170
26. Srinivasan C., Chellamani A., and Kuthalingam P. J. Org. Chem. 47 (1982) 428
27. Srinivasan C., Chellamani A., and Rajagopal S. J. Org. Chem. 50 (1985) 1201
28. Pryor W.A., and Hendrichson Jr. W.H. J. Am. Chem. Soc. 105 (1983) 7114
29. Rajasekaran K., Baskaran T., and Gnanasekaran C. J. Chem. Soc., Perkin Trans. 2 (1984) 1183
30. Miller A.E., Bischoff J.J., Bizub C., Luminoso P., and Smiley S. J. Am. Chem. Soc. 108 (1986) 7773
31. Davis F.A., McCanley J.P., Chattopachayay S., Herakai M., Towson J.C., Waston W.H., and Taranaiepour R. J. Am. Chem. Soc. 109 (1987) 3370
32. Watanabe Y., Iyanagi T., and Oae S. Tetrahedron Lett. 21 (1980) 3685
33. Watanabe Y., Numuta T., Iyanagi T., and Oae S. Bull. Chem. Soc. Jpn. 54 (1981) 1163
34. Oae S., Watanabe Y., and Fujimori K. Tetrahedron Lett. 23 (1982) 1189
35. Lee D.G., and Chen T. J. Org. Chem. 53 (1991) 5346
36. Baciocchi E., Intini D., Piermattei A., Roh C., and Ruzziconi R. Gazz. Chim. Ital. 119 (1989) 649
37. Arocoria A., Ballistreri F.P., Spina E., Tomaselli G.A., and Toscaon R.M. Gazz. Chim. Ital. 120 (1990) 309
38. Balakumar S., Thanasekaran P., Rajagopal S., and Ramaraj R. Tetrahedron 51 (1995) 4801
39. Ganesan T.K., Rajagopal S., Bharathy J.B., and Sheriff A.I.M. J. Org. Chem. 63 (1998) 21
40. Goto Y., Matsui T., Ozaki S., Watanabe Y., and Fukuzumi S. J. Am. Chem. Soc. 121 (1999) 9497
41. Pasto D.J., and Kent R. J. Org. Chem. 30 (1965) 2684
42. Webb K.S. Tetrahedron Lett. 35 (1994) 3457
43. Srinivasan C., and Pitchumani K. Indian J. Chem. 17A (1979) 162
44. Panigrahi G.P., and Nayak R.N. Curr. Sci. 49 (1980) 740
45. Srinivasan C., and Pitchumani K. Int. J. Chem. Kinet. 14 (1982) 789
46. Srinivasan C., and Pitchumani K. Bull. Chem. Soc. Jpn. 55 (1982) 289
47. Gurumurthy R., Gopalakrishnan M., and Sathiyanarayanan K. Tetrahedron 50 (1994) 13731
48. Kabilan S., Krishnasamy K., Sankar P., and Ganapathy A. Afinidad 52 (1995) 255
49. Thenraja D., Subramaniam P., and Srinivasan C. J. Chem. Soc., Perkin Trans. 2 (2002) 2125
50. Read J.F., Griffiths B.H.B., Lynch L.L., Maccormick K.J., and ChiuTam N.G.A. Inorg. React. Mech. 5 (2004) 135
51. Srinivasan C., Subramaniam P., and Chellamani A. Indian J. Chem. Sci. 3 (1989) 61
52. Srinivasan C., and Subramaniam P. J. Chem. Soc., Perkin Trans. 2 (1990) 1061
53. Johnson C.D. Tetrahedron 36 (1980) 3461 and references cited therein
54. Exner O. J. Chem. Soc., Perkin Trans. 2 (1993) 973
55. Saltzman H., and Sharefkin J.G. Organic Synthesis vol. 5 (1973), John Wiley and Sons, New York p. 658
56. Linde C., Akermark B., Norrby P.O., and Svensson M. Angew. Chem. Int. Ed. Engl. 121 (1999) 5083
57. Groves J.T., Lee J., and Marla S.S. J. Am. Chem. Soc. 119 (1997) 6269
58. Mac Donnel F.M., Fackler N.L.P., Stern C., and Halloran T.V.O. J. Am. Chem. Soc. 116 (1994) 7431
59. Feichtinger D., and Plattner D.A. Angew. Chem. Int. Ed. Engl. 36 (1997) 1718
60. Samsel E.G., Srinivasan K., and Kochi J.K. J. Am. Chem. Soc. 107 (1985) 7606
61. Righter B., SriHari S., Hunter S., and Masnovi J. J. Am. Chem. Soc. 115 (1993) 3918
62. Dufour M.N., Crumbliss A.L., Johnson G., and Gaudemer A. J. Mol. Catal. 7 (1980) 277
63. Castellino A.J., and Bruice T.C. J. Am. Chem. Soc. 110 (1988) 158
64. Groves J.T., and Watanabe Y. J. Am. Chem. Soc. 108 (1986) 507
65. Groves J.T., and Stern M.K. J. Am. Chem. Soc. 110 (1988) 8628
66. March J. Advanced Organic Chemistry. fourth ed. (1992), John Wiley and Sons, New York p. 215
67. Johnson C.D. Hammett Equation (1980), Cambridge University Press, New York
68. Bansal V., Sharma P.K., and Banerji K.K. Indian J. Chem. 39A (2000) 654
69. Kumbhat V., Sharma P.K., and Banerji K.K. J. Chem. Res. (S) (2001) 179