Selective organic synthesis over metal cation-exchanged clay catalyst

Sekiyu Gakkaishi (Journal of the Japan Petroleum Institute)

Volumn 40, Issue 5, 1997, Pages 329-341

  Tateiwa, Jun Ichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000143072     PISSN: 05824664     EISSN: None     Source Type: Journal    
DOI: 10.1627/jpi1958.40.329     Document Type: Article

References (93)

1. For recent reviews on organic reactions in the presence of clay catalysts, see for examples: Cornélis, A., Laszlo, P., Zettler, M. W., "Encyclopedia of Reagents for Organic Synthesis," ed. by Paquette, L. A., Wiley, Chichester (1995), Vol. 5, p. 3667-3671; Clark, J. H., "Catalysis of Organic Reaction Using Supported Inorganic Reagents," VCH, New York (1994); Izumi, Y., Urabe, K., Onaka, M., "Zeolite, Clay, and Heteropoly Acid in Organic Reactions," VCH, New York (1992).
2. For recent reviews on organic reactions in the presence of clay catalysts, see for examples: Cornélis, A., Laszlo, P., Zettler, M. W., "Encyclopedia of Reagents for Organic Synthesis," ed. by Paquette, L. A., Wiley, Chichester (1995), Vol. 5, p. 3667-3671; Clark, J. H., "Catalysis of Organic Reaction Using Supported Inorganic Reagents," VCH, New York (1994); Izumi, Y., Urabe, K., Onaka, M., "Zeolite, Clay, and Heteropoly Acid in Organic Reactions," VCH, New York (1992).
3. For recent reviews on organic reactions in the presence of clay catalysts, see for examples: Cornélis, A., Laszlo, P., Zettler, M. W., "Encyclopedia of Reagents for Organic Synthesis," ed. by Paquette, L. A., Wiley, Chichester (1995), Vol. 5, p. 3667-3671; Clark, J. H., "Catalysis of Organic Reaction Using Supported Inorganic Reagents," VCH, New York (1994); Izumi, Y., Urabe, K., Onaka, M., "Zeolite, Clay, and Heteropoly Acid in Organic Reactions," VCH, New York (1992).
4. a) Tateiwa, J., Horiuchi, H., Hashimoto, K., Yamauchi, T., Uemura, S., J. Org. Chem., 59, 5901 (1994)
5. b) Tateiwa, J., Nishimura, T., Horiuchi, H., Uemura, S., J. Chem. Soc., Perkin Trans. 1, 3367 (1994)
6. c) Tateiwa, J., Hayama, E., Nishimura, T., Uemura, S., Chem. Lett., 59 (1996)
7. d) Tateiwa, J., Horiuchi, H., Uemura, S., J. Org. Chem., 60, 4039 (1995)
8. e) Tateiwa, J., Uemura, S., Bull. Chem. Soc. Jpn., 69, 236 (1996).
9. f) Tateiwa, J., Horiuchi, H., Suama, M., Uemura, S., Bull. Chem. Soc. Jpn., 67, 2883 (1994).
10. a) Tateiwa, J., Horiuchi, H., Uermura, S., J. Chem. Soc., Chem. Commun., 2567 (1994)
11. b) Tateiwa, J., Horiuchi, H., Uemura, S., J. Chem. Soc., Perkin Trans. 2, 2013 (1995).
12. Ballantine, J. A., "Solid supports and Catalysts in Organic Synthesis," ed. by Smith, K., Ellis Horwood, London (1992), Part 2, Chap. 4, p. 101-102.
13. Clark, J. H., Macquarrie, D. J., Chem. Soc. Rev., 303 (1996).
14. Technical Information Bulletin AL-143, Aldrich Chemical Co., Inc., (1987).
15. 4+-Mont has a porous structure.
16. 4+-Mont has a porous structure.
17. 4+-Mont has a porous structure.
18. 4+-Mont has a porous structure.
19. Laszlo, P., Mathy, A., Helv. Chim. Acta, 70, 577 (1987).
20. Fischer, R., Koernig, W., Ger. Offen. 2 145 308 (1973); Chem. Abstr. ,78, 147566h (1973).
21. Chisso Corp., Jpn. Pat. 80 151 530 (1980); Chem. Abstr., 94, 156532b (1981).
22. Goudie, A. C., Gaster, L. M., Lake, A. W., Rose, C. J., Freeman, P. C., Hughes, B. O., Miller, D., J. Med. Chem., 21, 1260 (1978).
23. Fiege, H., Voges, H.-W., "Ullmann's Encyclopedia of Industrial Chemistry," 5th ed., eds. by Elvers, B., Hawkins, S., Schulz, G., VCH, Weinheim (1991), Vol. A19, p. 313-342.
24. Fujita, T., Ishiguro, M., Takahata, K., Saeki, K., Jpn. Pat. 85 252 444 (1985); Chem. Abstr., 104, 168144q (1986); Pitchumani, K., Pandian, A., J. Chem. Soc., Chem. Commun., 1613 (1990).
25. Fujita, T., Ishiguro, M., Takahata, K., Saeki, K., Jpn. Pat. 85 252 444 (1985); Chem. Abstr., 104, 168144q (1986); Pitchumani, K., Pandian, A., J. Chem. Soc., Chem. Commun., 1613 (1990).
26. Dauben, W. G., Cogen, J. M., Behar, V., Tetrahedron Lett., 31, 3241 (1990).
27. a) Hartmann, C. Gattermann, L., Chem. Ber., 25, 3531 (1892)
28. b) Sprung, M. M., Wallis, E.S., J. Am. Chem. Soc., 56, 1715 (1934)
29. c) Spanninger, P. A., von Rosenberg, J. L., J. Chem. Soc., Chem. Commun., 795 (1970)
30. d) Spanninger, P. A., von Rosenberg, J. L., J. Am. Chem. Soc., 94, 1970 (1972)
31. e) Spanninger, P. A., von Rosenberg, J. L., J. Am. Chem. Soc., 94, 1973 (1972) and references cited therein.
32. For example, see: March, J., "Advanced Organic Chemistry," 4th ed., Wiley, New York (1992), Chap. 11, p. 556-557.
33. For example, see: Hofmann, J. E., Schriesheim, A., "Friedel-Crafts and Related Reactions," ed. by Olah, G. A., Wiley, New York (1964), Vol. 2, Chap. 19, p. 597-640. For the preparation of bisphenol from phenol and formaldehyde or acetone in the presence of montmorillonite, see: Herdieckerhoff, E., Sutter, W., Ger. Offen. 1 051 864 (1959); Chem. Abstr., 55, 5432c (1961); Sun, K. K., U.S. Pat 4 052 466 (1977); Chem. Abstr., 87, 201086c (1977).
34. For example, see: Hofmann, J. E., Schriesheim, A., "Friedel-Crafts and Related Reactions," ed. by Olah, G. A., Wiley, New York (1964), Vol. 2, Chap. 19, p. 597-640. For the preparation of bisphenol from phenol and formaldehyde or acetone in the presence of montmorillonite, see: Herdieckerhoff, E., Sutter, W., Ger. Offen. 1 051 864 (1959); Chem. Abstr., 55, 5432c (1961); Sun, K. K., U.S. Pat 4 052 466 (1977); Chem. Abstr., 87, 201086c (1977).
35. For example, see: Hofmann, J. E., Schriesheim, A., "Friedel-Crafts and Related Reactions," ed. by Olah, G. A., Wiley, New York (1964), Vol. 2, Chap. 19, p. 597-640. For the preparation of bisphenol from phenol and formaldehyde or acetone in the presence of montmorillonite, see: Herdieckerhoff, E., Sutter, W., Ger. Offen. 1 051 864 (1959); Chem. Abstr., 55, 5432c (1961); Sun, K. K., U.S. Pat 4 052 466 (1977); Chem. Abstr., 87, 201086c (1977).
36. a) Niederl, J. B., Niederl, V., Shapiro, S., McGreal, M. E., J. Am. Chem. Soc., 59, 1113 (1937)
37. b) von Dianin, A., Zh. Russ. Fiz.-Khan. Obshchest, 23, 523 (1891); Chem. Ber., 25, 334 (1892)
38. b) von Dianin, A., Zh. Russ. Fiz.-Khan. Obshchest, 23, 523 (1891); Chem. Ber., 25, 334 (1892)
39. c) v. Braun, J., Liebigs Ann. Chem., 507, 15 (1933)
40. d) McGreal, M. E., Niederl, V., Niederl, J. B., J. Am. Chem. Soc., 61, 345 (1939).
41. Tsukervanik, I. P., Nazarova, Z. N., Zh. Obshch. Khim., 9, 33 (1939); Chem. Abstr., 33, 6265 (1939).
42. Tsukervanik, I. P., Nazarova, Z. N., Zh. Obshch. Khim., 9, 33 (1939); Chem. Abstr., 33, 6265 (1939).
43. Ref. 2c) and also Tateiwa, J., Hayama, E., Nishimura, T., Uemura, S., J. Chem. Soc., Perkin Trans. 1, 1923 (1997).
44. Hashimoto, Y., Hirata, K., Kihara, N., Hasegawa, M., Saigo, K., Tetrahedron Lett., 33, 6351 (1992); Hashimoto, Y., Hirata, K., Kagoshima, H., Kihara, N., Hasegawa, M., Saigo, K., Tetrahedron, 49, 5969 (1993).
45. Hashimoto, Y., Hirata, K., Kihara, N., Hasegawa, M., Saigo, K., Tetrahedron Lett., 33, 6351 (1992); Hashimoto, Y., Hirata, K., Kagoshima, H., Kihara, N., Hasegawa, M., Saigo, K., Tetrahedron, 49, 5969 (1993).
46. Roberts, R. M., Khalaf, A. A., "Friedel-Crafts Alkylation Chemistry," Marcel Dekker, New York (1984), Chap. 8, p. 701-762: Saito, S., Ohwada T., Shudo, K., J. Am. Chem. Soc., 117, 11081 (1995).
47. Roberts, R. M., Khalaf, A. A., "Friedel-Crafts Alkylation Chemistry," Marcel Dekker, New York (1984), Chap. 8, p. 701-762: Saito, S., Ohwada T., Shudo, K., J. Am. Chem. Soc., 117, 11081 (1995).
48. As examples for the aromatic alkylation of phenol with aldehydes in the presence of hydrogen to produce alkylphenols, see: Smith, W. E. U.S. Pat. 4 048 239 (1977); Chem. Abstr., 88, 6545v (1978); Takahashi, E., Ozaki, K., Jpn. Pat. 88 230 648 (1988); Chem. Abstr., 110, 38742w (1989).
49. As examples for the aromatic alkylation of phenol with aldehydes in the presence of hydrogen to produce alkylphenols, see: Smith, W. E. U.S. Pat. 4 048 239 (1977); Chem. Abstr., 88, 6545v (1978); Takahashi, E., Ozaki, K., Jpn. Pat. 88 230 648 (1988); Chem. Abstr., 110, 38742w (1989).
50. Greene, T. W., Wuts, P. G. M., "Protective Groups in Organic Synthesis," 2nd ed., Wiley, New York (1991), Chap. 4, p. 175-210.
51. Thuy, V. M., Maitte, P., Bull. Soc. Chim. Fr., 2558 (1975); Taylor, E. C., Chiang, C.-S., Synthesis, 467 (1977).
52. Thuy, V. M., Maitte, P., Bull. Soc. Chim. Fr., 2558 (1975); Taylor, E. C., Chiang, C.-S., Synthesis, 467 (1977).
53. Patwardhan, S. A., Dev, S., Synthesis, 348 (1974); Olah, G. A., Narang, S. C., Meidar, D., Salem, G. F., Synthesis, 282 (1981).
54. Patwardhan, S. A., Dev, S., Synthesis, 348 (1974); Olah, G. A., Narang, S. C., Meidar, D., Salem, G. F., Synthesis, 282 (1981).
55. Corma, A., Climent, M. J., Carcia, H., Primo, J., Appl. Catal., 59, 333 (1990).
56. a) Balogh, M., Laszlo, P., "Organic Chemistry Using Clays," Springer-Verlag, New York (1993), Chap. 14, p. 140-143
57. b) Heinemann, H., U.S. Pat. 2 451 949 (1948); Chem. Abstr., 43, 2222c (1949)
58. c) Lorette, N. B., Howard, W. L., Brown Jr., J. H., J. Org. Chem., 24, 1731 (1959)
59. d) Lambert, P., Ind. Chim. Belgr, 26, 1012 (1961); Chem. Abstr., 56, 5822h (1962)
60. d) Lambert, P., Ind. Chim. Belgr, 26, 1012 (1961); Chem. Abstr., 56, 5822h (1962)
61. e) Ballantine, J. A., Purnell, J. H., Thomas, J. M., Clay Miner., 18, 347 (1983)
62. f) Joshi, M. V., Narasimhan, C. S., J. Catal., 120, 282 (1989).
63. For examples, see: Crabtree, R. H., Habib, A., "Comprehensive Organic Synthesis," eds. by Trost, B. M., Fleming, I., Ley, S. V., Pergamon Press, Oxford (1991), Vol. 7, Chap. 1.1, p. 10-14 and references cited therein; Barton, D. H. R., Chem. Soc. Rev., 237 (1996); Cook, G. K., Mayer, J. M., J. Am. Chem. Soc., 117, 7139 (1995) and references cited therein; Nomura, K., Uemura, S., J. Chem. Soc., Chem. Commun., 129 (1994); Murahashi, S., Oda, Y., Komiya, N., Naota, T., Tetrahedron Lett., 35, 7953 (1994); Ménage, S., Collomb-Dunand-Sauthier, M.-N., Lambeaux, C., Fontecave, M., J. Chem. Soc., Chem. Commun., 1885 (1994).
64. For examples, see: Crabtree, R. H., Habib, A., "Comprehensive Organic Synthesis," eds. by Trost, B. M., Fleming, I., Ley, S. V., Pergamon Press, Oxford (1991), Vol. 7, Chap. 1.1, p. 10-14 and references cited therein; Barton, D. H. R., Chem. Soc. Rev., 237 (1996); Cook, G. K., Mayer, J. M., J. Am. Chem. Soc., 117, 7139 (1995) and references cited therein; Nomura, K., Uemura, S., J. Chem. Soc., Chem. Commun., 129 (1994); Murahashi, S., Oda, Y., Komiya, N., Naota, T., Tetrahedron Lett., 35, 7953 (1994); Ménage, S., Collomb-Dunand-Sauthier, M.-N., Lambeaux, C., Fontecave, M., J. Chem. Soc., Chem. Commun., 1885 (1994).
65. For examples, see: Crabtree, R. H., Habib, A., "Comprehensive Organic Synthesis," eds. by Trost, B. M., Fleming, I., Ley, S. V., Pergamon Press, Oxford (1991), Vol. 7, Chap. 1.1, p. 10-14 and references cited therein; Barton, D. H. R., Chem. Soc. Rev., 237 (1996); Cook, G. K., Mayer, J. M., J. Am. Chem. Soc., 117, 7139 (1995) and references cited therein; Nomura, K., Uemura, S., J. Chem. Soc., Chem. Commun., 129 (1994); Murahashi, S., Oda, Y., Komiya, N., Naota, T., Tetrahedron Lett., 35, 7953 (1994); Ménage, S., Collomb-Dunand-Sauthier, M.-N., Lambeaux, C., Fontecave, M., J. Chem. Soc., Chem. Commun., 1885 (1994).
66. For examples, see: Crabtree, R. H., Habib, A., "Comprehensive Organic Synthesis," eds. by Trost, B. M., Fleming, I., Ley, S. V., Pergamon Press, Oxford (1991), Vol. 7, Chap. 1.1, p. 10-14 and references cited therein; Barton, D. H. R., Chem. Soc. Rev., 237 (1996); Cook, G. K., Mayer, J. M., J. Am. Chem. Soc., 117, 7139 (1995) and references cited therein; Nomura, K., Uemura, S., J. Chem. Soc., Chem. Commun., 129 (1994); Murahashi, S., Oda, Y., Komiya, N., Naota, T., Tetrahedron Lett., 35, 7953 (1994); Ménage, S., Collomb-Dunand-Sauthier, M.-N., Lambeaux, C., Fontecave, M., J. Chem. Soc., Chem. Commun., 1885 (1994).
67. For examples, see: Crabtree, R. H., Habib, A., "Comprehensive Organic Synthesis," eds. by Trost, B. M., Fleming, I., Ley, S. V., Pergamon Press, Oxford (1991), Vol. 7, Chap. 1.1, p. 10-14 and references cited therein; Barton, D. H. R., Chem. Soc. Rev., 237 (1996); Cook, G. K., Mayer, J. M., J. Am. Chem. Soc., 117, 7139 (1995) and references cited therein; Nomura, K., Uemura, S., J. Chem. Soc., Chem. Commun., 129 (1994); Murahashi, S., Oda, Y., Komiya, N., Naota, T., Tetrahedron Lett., 35, 7953 (1994); Ménage, S., Collomb-Dunand-Sauthier, M.-N., Lambeaux, C., Fontecave, M., J. Chem. Soc., Chem. Commun., 1885 (1994).
68. For examples, see: Crabtree, R. H., Habib, A., "Comprehensive Organic Synthesis," eds. by Trost, B. M., Fleming, I., Ley, S. V., Pergamon Press, Oxford (1991), Vol. 7, Chap. 1.1, p. 10-14 and references cited therein; Barton, D. H. R., Chem. Soc. Rev., 237 (1996); Cook, G. K., Mayer, J. M., J. Am. Chem. Soc., 117, 7139 (1995) and references cited therein; Nomura, K., Uemura, S., J. Chem. Soc., Chem. Commun., 129 (1994); Murahashi, S., Oda, Y., Komiya, N., Naota, T., Tetrahedron Lett., 35, 7953 (1994); Ménage, S., Collomb-Dunand-Sauthier, M.-N., Lambeaux, C., Fontecave, M., J. Chem. Soc., Chem. Commun., 1885 (1994).
69. For examples, see: a) Barloy, L. Lallier, J. P., Battioni, P., Mansuy, D., Piffard, Y., Tournoux, M., Valim, J. B., Jones, W., New J. Chem., 16, 71 (1992) b) Hashimoto, K., Asahi, Y., Maki, T., Jpn. Pat. 88 303 936 (1988); Chem. Abstr., 111, 6957z (1989) c) Herron, N., New J. Chem., 13, 761 (1989) d) Rao, P. R. H. P., Ramaswamy, A. V., J. Chem. Soc., Chem. Commun., 1245 (1992) and references cited therein.
70. For examples, see: a) Barloy, L. Lallier, J. P., Battioni, P., Mansuy, D., Piffard, Y., Tournoux, M., Valim, J. B., Jones, W., New J. Chem., 16, 71 (1992) b) Hashimoto, K., Asahi, Y., Maki, T., Jpn. Pat. 88 303 936 (1988); Chem. Abstr., 111, 6957z (1989) c) Herron, N., New J. Chem., 13, 761 (1989) d) Rao, P. R. H. P., Ramaswamy, A. V., J. Chem. Soc., Chem. Commun., 1245 (1992) and references cited therein.
71. For examples, see: a) Barloy, L. Lallier, J. P., Battioni, P., Mansuy, D., Piffard, Y., Tournoux, M., Valim, J. B., Jones, W., New J. Chem., 16, 71 (1992) b) Hashimoto, K., Asahi, Y., Maki, T., Jpn. Pat. 88 303 936 (1988); Chem. Abstr., 111, 6957z (1989) c) Herron, N., New J. Chem., 13, 761 (1989) d) Rao, P. R. H. P., Ramaswamy, A. V., J. Chem. Soc., Chem. Commun., 1245 (1992) and references cited therein.
72. For examples, see: a) Barloy, L. Lallier, J. P., Battioni, P., Mansuy, D., Piffard, Y., Tournoux, M., Valim, J. B., Jones, W., New J. Chem., 16, 71 (1992) b) Hashimoto, K., Asahi, Y., Maki, T., Jpn. Pat. 88 303 936 (1988); Chem. Abstr., 111, 6957z (1989) c) Herron, N., New J. Chem., 13, 761 (1989) d) Rao, P. R. H. P., Ramaswamy, A. V., J. Chem. Soc., Chem. Commun., 1245 (1992) and references cited therein.
73. Dolaude, L., Laszlo, P., Lehance, P., Tetrahedron Lett., 36, 8505 (1995); Dalaude, L., Laszlo, P., J. Org. Chem., 61, 6360 (1996).
74. Dolaude, L., Laszlo, P., Lehance, P., Tetrahedron Lett., 36, 8505 (1995); Dalaude, L., Laszlo, P., J. Org. Chem., 61, 6360 (1996).
75. For a recent example see: Murahashi, S., Angew. Chem., Int. Ed. Engl., 34, 2443 (1995) and references cited therein.
76. a) Kawai, M., Onaka, M., Izumi, Y., Chem. Lett., 1581 (1986)
77. b) Onaka, M., Ono, R., Kawai, M., Izumi, Y., Bull. Chem. Soc. Jpn., 60, 2688 (1987)
78. c) Kawai, M., Onaka, M., Izumi, Y., Bull. Chem. Soc. Jpn., 61, 1237 (1988).
79. a) Kawai, M., Onaka, M., Izumi, Y., J. Chem. Soc., Chem. Commun. 1203 (1987)
80. b) Kawai, M., Onaka, M., Izumi, Y., Bull. Chem. Soc. Jpn., 61, 2157 (1988).
81. For example, see: a) Laszlo, P., Lucchetti, J., Tetrahedron Lett., 25, 1567 (1984) b) Laszlo, P., Lucchetti, J., Tetrahedron Lett., 25, 2147 (1984) c) Lazlo, P., Lucchetti, J., Tetrahedron Lett., 25, 4387 (1984).
82. For example, see: a) Laszlo, P., Lucchetti, J., Tetrahedron Lett., 25, 1567 (1984) b) Laszlo, P., Lucchetti, J., Tetrahedron Lett., 25, 2147 (1984) c) Lazlo, P., Lucchetti, J., Tetrahedron Lett., 25, 4387 (1984).
83. For example, see: a) Laszlo, P., Lucchetti, J., Tetrahedron Lett., 25, 1567 (1984) b) Laszlo, P., Lucchetti, J., Tetrahedron Lett., 25, 2147 (1984) c) Lazlo, P., Lucchetti, J., Tetrahedron Lett., 25, 4387 (1984).
84. For example, March, J., "Advanced Organic Chemistry," 4th ed, Wiley, New York (1992), Chap. 16, p. 967-968 and references cited therein.
85. Sakamoto, T., Kondo, Y., Yamanaka, H., Tetrahedron Lett., 33, 6845 (1992).
86. For a review of Prins reactions and carbonyl-ene reactions, see: Snider, B. B., "Comprehensive Organic Synthesis," ed. by Trost, B. M., Fleming, I., Heathcock, C. H., Pergamon Press, Oxford (1991), Vol. 2, Chap. 2.1, p. 527-561 and references cited therein.
87. For examples, a) Delmas, M., Gaset, A., Synthesis, 871 (1980) b) Gharbi, R. E., Delmas, M., Gaset, A., Synthesis, 361 (1981) c) Delmas, M., Gaset, A.,J.Mol. Catal., 17, 35 and 51 (1982).
88. For examples, a) Delmas, M., Gaset, A., Synthesis, 871 (1980) b) Gharbi, R. E., Delmas, M., Gaset, A., Synthesis, 361 (1981) c) Delmas, M., Gaset, A.,J.Mol. Catal., 17, 35 and 51 (1982).
89. For examples, a) Delmas, M., Gaset, A., Synthesis, 871 (1980) b) Gharbi, R. E., Delmas, M., Gaset, A., Synthesis, 361 (1981) c) Delmas, M., Gaset, A.,J.Mol. Catal., 17, 35 and 51 (1982).
90. For example, Kobzar', E. A., Korchagina, D. V., Salakhutdinov, N. F., Ione, K. G., Barkhash, V. A., J. Org. Chem. USSR (Engl. Transl.), 28, 1030 (1992).
91. a) Roudier, J.-F., Foucaud, A., Tetrahedron Lett., 23, 4375 (1984)
92. b) Ballantine, J. A., "Solid Supports and Catalysts in Organic Synthesis," ed. by Smith, K., Ellis Horwood, London (1992), Part 2, Chap. 4, p. 106.
93. Tateiwa, J., Kimura, A., Takasuka, M., Uemura, S., J. Chem. Soc., Perkin Trans. 1, in press.