Regiospecific aromatic chlorination of alkyl phenyl ethers using sodium chlorite catalysed by manganese(III) acetylacetonate and moist alumina in dichloromethane

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1997, Pages 3081-3085

  Hirano, Masao ^a   Yakabe, Shigetaka ^a   Monobe, Hiroyuki ^a   Clark, James H ^b   Morimoto, Takashi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748647667     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a701813d     Document Type: Article

References (69)

1. Reviews are available: H. Heavy, in Comprehensive Organic Chemistry, ed. D. H. R. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, vol. 1, p. 291;
2. P. B. D. de la Mare, Acc. Chem. Res., 1974, 7, 361;
3. J. March, Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 4th edn., John Wiley & Sons, New York, 1992, p. 531-534;
4. E. B. Merkushev, Synthesis, 1988, 923;
5. D. E. Pearson and C. A. Buehler, Synthesis, 1971, 455;
6. R. Taylar, Electrophilic Aromatic Substitution, John Wiley & Sons, Chichester, 1990, ch. 9.
7. Speciality Chemicals, ed. B. Pearson, Elsevier Applied Science, London, 1991, p. 15-93.
8. For recent aromatic chlorinations, see: H. A. Muathen, Tetrahedron, 1996, 52, 8863;
9. R. Breslow, Acc. Chem. Res., 1995, 28, 146;
10. S. M. Hubig, W. Jung and J. K. Kochi, J. Am. Chem. Soc., 1994, 116, 6233;
11. R. Rathore, S. H. Loyd and J. K. Kochi, J. Am. Chem. Soc., 1994, 116, 8414;
12. Y. Goldberg and H. Alper, J. Org. Chem., 1993, 58, 3072;
13. F. Bellesia, F. Ghelfi, U. M. Pagnoni and A. Pinetti, J. Chem. Res., 1991, (S), 284;
14. J. G. Lee, H. T. Cha, U. C. Yon, Y. S. Suh, K. C. Kim and I. S. Park, Bull. Korean Chem. Soc., 1991, 12, 4;
15. L. Delaude and P. Laszlo, Catal. Lett., 1990, 5, 35;
16. K. H. Chung, H. J. Kim, H. R. Kirn and E. K. Ryu, Synth. Commun., 1990, 20, 2991;
17. K. Smith, M. Butters and B. Nay, Synthesis, 1985, 1157;
18. K. Smith, M. Butters, W. E. Paget and B. Nay, Synthesis, 1985, 1155;
19. N. Kamigata, T. Satoh, M. Yoshida, H. Matsuyama and M. Kameyama, Bull. Chem. Soc. Jpn., 1989, 61, 2226;
20. F. Minisci, E. Vismara and F. Fontana, J. Chem. Soc., Perkin Trans. 2, 1989, 123;
21. K. Shibata, Y. Itoh, N. Tokitoh, R. Okazaki and N. Inamoto, Bull. Chem. Soc. Jpn., 1991, 64, 3749;
22. K. Smith, M. Butters and B. Nay, Tetrahedron Lett., 1988, 29, 1319;
23. J. R. Lindsay Smith, L. C. McKeer and J. M. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, 1533;
24. J. R. Lindsay Smith, L. C. McKeer and J. M. Taylor, J. Chem. Soc., Perkin Trans. 2, 1988, 385;
25. J. R. Lindsay Smith, L. C. McKeer and J. M. Taylor, J. Chem. Soc., Perkin Trans. 2, 1989, 1529;
26. J. R. Lindsay Smith, L. C. McKeer and J. M. Taylor, J. Chem. Soc., Perkin Trans. 2, 1989, 1537;
27. S. Kajigaeshi, Y. Shinmasu, S. Fujisaki and T. Kakinami, Chem. Lett., 1989, 415;
28. G. A. Olah, L. Ohannesian and M. Arvanaghi, Synthesis, 1986, 868;
29. W. D. Watson, J. Org Chem., 1985, 50, 2145;
30. T. E. Nickson and C. A. Roche-Dolson, Synthesis, 1985, 669;
31. H. Konishi, K. Yokota, Y. Ichihashi, T. Okano and J. Kiji, Chem. Lett., 1980, 1423; ref. 11b.
32. For comprehensive reviews on supported reagent chemistry, see: (a) J. H. Clark, Catalysis of Organic Reactions by Supported Inorganic Reagents, VCH, New York, 1994;
33. (b) J. H. Clark, A. P. Kybett and D. J. Macquarrie, Supported Reagents. Preparation, Analysis and Applications, VCH, New York, 1992;
34. (c) J. H. Clark and T. W. Bastock, in ref. 2, p. 383;
35. (d) Preparative Chemistry Using Supported Reagents, ed. P. Laszlo, Academic Press, San Diego, 1987;
36. (e) Solid Supports and Catalysis in Organic Synthesis, ed. K. Smith, Ellis Horwood, Chichester, 1992;
37. (f) Organic Chemistry Using Clays, ed. M. Balogh and P. Laszlo, Springer-Verlag, Berlin, 1993.
38. J. H. Clark and D. J. Macquarrie, Chem. Soc. Rev., 1996, 303;
39. Chemistry of Waste Minimization, ed. J. H. Clark, Chapman and Hall, London, 1995;
40. T. W. Bastock and J. H. Clark, in ref. 2, p. 383-396.
41. L. Delaude, P. Laszlo and K. Smith, Acc. Chem. Res., 1993, 26, 607.
42. M. E. Davis. Acc. Chem. Res., 1993, 26, 111.
43. M. Hirano, S. Yakabe, J. H. Clark and T. Morimoto, J. Chem. Soc., Perkin Trans. 1, 1996, 2693.
44. M. Kodomari, S. Takahashi and S. Yoshitomi, Chem. Lett., 1987, 1901.
45. M. Hirano, S. Yakabe, J. H. Clark, H. Kudo and T. Morimoto, Synth. Commun., 1996, 26, 1875.
46. (a) T. Nishiguchi and F. Asano, J. Org. Chem., 1989, 54, 1531;
47. (b) M. Kodomari, H. Satoh and S. Yoshitomi, Bull. Chem. Soc Jpn., 1988, 61, 4149;
48. (c) S. Yasui, M. Fujii, K. Nakamura and A. Ohno, Bull. Chem. Soc. Jpn., 1987, 60, 963;
49. (d) M. O. Brimeyer, A. Mehrota, S. Quid, A. Nigam and S. L. Regen, J. Org. Chem., 1980, 45, 4254;
50. (e) F. M. Menger and C. Lee, J. Org. Chem., 1979, 44, 3446;
51. (f) E. Keinan and Y. Mazur, J. Org. Chem., 1978, 43, 1020;
52. M. Hojo and R. Masuda; (g) Synth. Commun., 1975, 5, 169;
53. (h) Tetrahedron Lett., 1976, 613;
54. (i) B. B. Jarvis and M. M. Evans, J. Org. Chem., 1974, 39, 643; refs. 7 and 9.
55. M. Onaka, K. Sugita and Y. Izumi, J. Org. Chem., 1989, 54, 1116;
56. T. Ando, T. Kawate, J. Yamawaki and T. Hanafusa, Chem. Lett., 1982, 935.
57. Similar explanation was given for the acceleration of reactions with the use of solid reagents by a small amount of water: L. A. Carpino and A. C. Sau, J. Chem. Soc., Chem. Commun., 1979, 514;
58. M. Tanaka and M. Koyanagi, Synthesis, 1981, 973; ref. 12.
59. L. Delaude and P. Laszlo, J. Org. Chem., 1990, 55, 5260;
60. D. Antenucci, L. Delaude, A. M. Fransolet and P. Laszlo, J. Catal., 1992, 135, 92; and references cited therein.
61. 10 and nuclear chlorination of aromatic ethers (unpublished data) in dichloromethane in the presence of moist alumina.
62. A large amount of (salen)manganese(III) complex catalysts (≤13 mol%) were frequently required because of, in part, destruction of them during the reactions: T. Nagata, K. Imagawa, T. Yamada and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1995, 68, 1455;
63. Chem. Lett., 1994, 1259;
64. T. Mukaiyama, T. Yamada, T. Nagata and K. Imagawa, Chem. Lett., 1993, 327;
65. R. Irie, K. Noda, Y. Ito, N. Matsumoto and T. Katsuki, Tetrahedron Lett., 1990, 31, 7345;
66. P. Pietikäinen, Tetrahedron Lett., 1994, 35, 941.
67. M. Siskin, G. Brons, A. R. Katritzky and R. Murugan, Energy Fuels, 1990, 4, 482.
68. R. A. Smith, J. Am. Chem. Soc., 1933, 55, 3718.
69. Technique of Organic Chemistry, Vol. II, Organic Solvents, ed. J. A. Ridick and W. B. Bunger, Wiley Interscience, New York, 3rd edn., 1970.