Cation-Exchanged Montmorillonite (Mn+-Mont)-Catalyzed Prins Reaction

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 8, 1996, Pages 2361-2368

  Tateiwa, Jun Ichi ^a   Hashimoto, Keiji ^b   Yamauchi, Takayoshi ^c   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

^b OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

^c Nissei Chemical Inc   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000629019     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.2361     Document Type: Article

References (52)

1. For recent reviews on the reactions in the presence of clays, see: A. Cornélis, P. Laszlo, and M. W. Zettler, in "Encyclopedia of Reagents for Organic Synthesis," ed by L. A. Paquette, Wiley, Chichester (1995), Vol. 5, pp. 3667-3671; A. Cornélls and P. Laszlo, Synlett, 1994, 155; J. H. Clark, "Catalysis of Organic Reactions Using Supported Inorganic Reagents," VCH, New York (1994); M. Balogh and P. Laszlo, "Organic Chemistry Using Clays," Springer-Verlag, New York (1993).
2. For recent reviews on the reactions in the presence of clays, see: A. Cornélis, P. Laszlo, and M. W. Zettler, in "Encyclopedia of Reagents for Organic Synthesis," ed by L. A. Paquette, Wiley, Chichester (1995), Vol. 5, pp. 3667-3671; A. Cornélls and P. Laszlo, Synlett, 1994, 155; J. H. Clark, "Catalysis of Organic Reactions Using Supported Inorganic Reagents," VCH, New York (1994); M. Balogh and P. Laszlo, "Organic Chemistry Using Clays," Springer-Verlag, New York (1993).
3. For recent reviews on the reactions in the presence of clays, see: A. Cornélis, P. Laszlo, and M. W. Zettler, in "Encyclopedia of Reagents for Organic Synthesis," ed by L. A. Paquette, Wiley, Chichester (1995), Vol. 5, pp. 3667-3671; A. Cornélls and P. Laszlo, Synlett, 1994, 155; J. H. Clark, "Catalysis of Organic Reactions Using Supported Inorganic Reagents," VCH, New York (1994); M. Balogh and P. Laszlo, "Organic Chemistry Using Clays," Springer-Verlag, New York (1993).
4. For recent reviews on the reactions in the presence of clays, see: A. Cornélis, P. Laszlo, and M. W. Zettler, in "Encyclopedia of Reagents for Organic Synthesis," ed by L. A. Paquette, Wiley, Chichester (1995), Vol. 5, pp. 3667-3671; A. Cornélls and P. Laszlo, Synlett, 1994, 155; J. H. Clark, "Catalysis of Organic Reactions Using Supported Inorganic Reagents," VCH, New York (1994); M. Balogh and P. Laszlo, "Organic Chemistry Using Clays," Springer-Verlag, New York (1993).
5. For recent papers, see: A. R. A. S. Deshmukh, V. K. Gumaste, and B. M. Bhawal, Synth. Commun., 25, 3939 (1995); M. Matsui and H. Yamamoto, Bull Chem. Soc. Jpn., 69, 137 (1996).
6. For recent papers, see: A. R. A. S. Deshmukh, V. K. Gumaste, and B. M. Bhawal, Synth. Commun., 25, 3939 (1995); M. Matsui and H. Yamamoto, Bull Chem. Soc. Jpn., 69, 137 (1996).
7. a) J. Tateiwa, H. Horiuchi, K. Hashimoto, T. Yamauchi, and S. Uemura, J. Org. Chem., 59, 5901 (1994)
8. b) J. Tateiwa, T. Nishimura, H. Horiuchi, and S. Uemura, J. Chem. Soc., Perkin Trans. I, 1994, 3367
9. c) J. Tateiwa, E. Hayama, T. Nishimura, and S. Uemura, Chem. Lett., 1996, 59
10. d) J. Tateiwa, H. Horiuchi, M. Suama, and S. Uemura, Bull. Chem. Soc. Jpn., 67, 2883 (1994);
11. e) J. Tateiwa, H. Horiuchi, and S. Uemura, J. Org. Chem., 60, 4039 (1995).
12. a) J. Tateiwa, H. Horiuchi, and S. Uemura, J. Chem. Soc., Chem. Commun., 1994, 2567
13. b) J. Tateiwa, H. Horiuchi, and S. Uemura, J. Chem. Soc., Perkin Trans. 2, 1995, 2013.
14. For example: J. March, "Advanced Organic Chemistry," 4th ed, Wiley, New York (1992), Chap. 16, pp. 967-968, and references cited therein.
15. T. Sakamoto, Y. Kondo, and H. Yamanaka, Tetrahedron Lett., 33, 6845 (1992).
16. For a review of Prins reactions and carbonyl ene reactions, see: B. B. Snider, "Comprehensive Organic Synthesis," ed by B. M. Trost, I. Fleming, and C. H. Heathcock, Pergamon Press, Oxford (1991), Vol. 2, Chap. 2.1, pp. 527-561, and references cited therein.
17. For examples: a) M. Delmas and A. Gaset, Synthesis, 1980, 871; b) R. E. Gharbi, M. Delmas, and A. Gaset, Synthesis, 1981, 361; c) M. Delmas and A. Gaset, J. Mol. Catal., 17, 35 and 51 (1982).
18. For examples: a) M. Delmas and A. Gaset, Synthesis, 1980, 871; b) R. E. Gharbi, M. Delmas, and A. Gaset, Synthesis, 1981, 361; c) M. Delmas and A. Gaset, J. Mol. Catal., 17, 35 and 51 (1982).
19. For examples: a) M. Delmas and A. Gaset, Synthesis, 1980, 871; b) R. E. Gharbi, M. Delmas, and A. Gaset, Synthesis, 1981, 361; c) M. Delmas and A. Gaset, J. Mol. Catal., 17, 35 and 51 (1982).
20. For example: E. A. Kobzar, D. V. Korchagina, N. F. Salakhutdinov, K. G. Ione, and V. A. Barkhash, J. Org. Chem. USSR (Engl. Transl.), 28, 1030 (1992).
21. M. Kawai, M. Onaka, and Y. Izumi, Bull. Chem. Soc. Jpn., 61, 1237 (1988); K. Higuchi, M. Onaka, and Y. Izumi, Bull. Chem. Soc. Jpn., 66, 2016 (1993).
22. M. Kawai, M. Onaka, and Y. Izumi, Bull. Chem. Soc. Jpn., 61, 1237 (1988); K. Higuchi, M. Onaka, and Y. Izumi, Bull. Chem. Soc. Jpn., 66, 2016 (1993).
23. J. A. Ballantine, "Solid Supports and Catalysts in Organic Synthesis," ed by K. Smith, Ellis Horwood, London (1992), Part 2, Chap. 4, pp. 101-102; F. J. A. Kellendonk, J. J. L. Heinerman, and R. A. van Santen, "Preparative Chemistry Using Supported Reagents," ed by P. Laszlo, Academic Press, New York (1987), Part 8, Chap. 23, pp. 456-457; J. M. Adams, "Preparative Chemistry Using Supported Reagents," ed by P. Laszlo, Academic Press, New York (1987), Part 8, Chap. 27, pp. 509-511.
24. J. A. Ballantine, "Solid Supports and Catalysts in Organic Synthesis," ed by K. Smith, Ellis Horwood, London (1992), Part 2, Chap. 4, pp. 101-102; F. J. A. Kellendonk, J. J. L. Heinerman, and R. A. van Santen, "Preparative Chemistry Using Supported Reagents," ed by P. Laszlo, Academic Press, New York (1987), Part 8, Chap. 23, pp. 456-457; J. M. Adams, "Preparative Chemistry Using Supported Reagents," ed by P. Laszlo, Academic Press, New York (1987), Part 8, Chap. 27, pp. 509-511.
25. J. A. Ballantine, "Solid Supports and Catalysts in Organic Synthesis," ed by K. Smith, Ellis Horwood, London (1992), Part 2, Chap. 4, pp. 101-102; F. J. A. Kellendonk, J. J. L. Heinerman, and R. A. van Santen, "Preparative Chemistry Using Supported Reagents," ed by P. Laszlo, Academic Press, New York (1987), Part 8, Chap. 23, pp. 456-457; J. M. Adams, "Preparative Chemistry Using Supported Reagents," ed by P. Laszlo, Academic Press, New York (1987), Part 8, Chap. 27, pp. 509-511.
26. J.-F. Roudier and A. Foucaud, Tetrahedron Lett., 25, 4375 (1984).
27. D. D. Perrin and W. L. F. Armarego, "Purification of Laboratory Chemicals," 3rd ed, Pergamon Press, Oxford (1988).
28. 2+-monts: K. Higuchi, M. Onaka, and Y. Izumi, Bull. Chem. Soc. Jpn., 66, 2016 (1993).
29. 2+-monts: K. Higuchi, M. Onaka, and Y. Izumi, Bull. Chem. Soc. Jpn., 66, 2016 (1993).
30. 2+-monts: K. Higuchi, M. Onaka, and Y. Izumi, Bull. Chem. Soc. Jpn., 66, 2016 (1993).
31. 3+-mont: Y. G. Ha, Taehan Hwahakhoe Chi (Korean), 30, 488 (1986); Chem. Abstr., 105, 214410u (1986).
32. 3+-mont: Y. G. Ha, Taehan Hwahakhoe Chi (Korean), 30, 488 (1986); Chem. Abstr., 105, 214410u (1986).
33. 3+-mont: Y. G. Ha, Taehan Hwahakhoe Chi (Korean), 30, 488 (1986); Chem. Abstr., 105, 214410u (1986).
34. 3+-mont: Y. G. Ha, Taehan Hwahakhoe Chi (Korean), 30, 488 (1986); Chem. Abstr., 105, 214410u (1986).
35. 3+-mont: Y. G. Ha, Taehan Hwahakhoe Chi (Korean), 30, 488 (1986); Chem. Abstr., 105, 214410u (1986).
36. 3+-mont: Y. G. Ha, Taehan Hwahakhoe Chi (Korean), 30, 488 (1986); Chem. Abstr., 105, 214410u (1986).
37. 3+-mont: Y. G. Ha, Taehan Hwahakhoe Chi (Korean), 30, 488 (1986); Chem. Abstr., 105, 214410u (1986).
38. M. M. Woyski and R. E. Harris, "Treatise on Analytical Chemistry," ed by I. M. Kolthoff, P. J. Elving, and E. B. Sandell, Wiley, New York (1963), Part 2, Vol. 8, pp. 28-36.
39. For example, see: R. W. Shortridge, J. Am. Chem. Soc., 70, 873 (1948).
40. J.-P. Durand, M. Davidson, M. Hellin, and F. Coussemant, Bull. Soc. Chim. Fr., 1970, 4355.
41. N. V. Shorygina, Zh. Obshch. Khim., 26, 1460 (1956); Chem. Abstr., 50, 14763g (1956).
42. N. V. Shorygina, Zh. Obshch. Khim., 26, 1460 (1956); Chem. Abstr., 50, 14763g (1956).
43. G. Ferrand and J. Huet, Bull. Soc. Chim. Fr., 1973, 3122.
44. For example, see: W. S. Emerson, J. Am. Chem. Soc., 72, 5314 (1950).
45. W. S. Emerson, J. Org. Chem., 10, 464 (1945).
46. M. T. Jernigan and E. L. Eliel, J. Am. Chem. Soc., 117, 9638 (1995).
47. P. D. Woodgate, S. J. Janssen, P. S. Rutledge, S. D. Woodgate, and R. C. Cambie, Synthesis, 1984, 1017.
48. M. Hojo, T. Ichi, and K. Shibato, J. Org. Chem., 50, 1478 (1985).
49. H. Staudinger and F. Breusch, Ber., 62, 442 (1929).
50. "Carbon-13 NMR spectral Data," 4th ed, ed by W. Bremser, L. Ernst, B. Franke, R. Gerhards, and A. Hardt, VCH, Weinheim (1987) (microfiches).
51. E. C. Friedrich and K. G. Runkle, J. Chem. Educ., 63, 127 (1986).
52. J. Delmau, J.-C. Duplan, and M. Davidson, Tetrahedron, 23, 4371 (1967).