The oxidation of alcohols in N-oxyl-immobilized silica gel/aqueous NaOCl disperse systems. A prominent access to a column-flow system

Bulletin of the Chemical Society of Japan

Volumn 77, Issue 9, 2004, Pages 1745-1755

  Tanaka, Hideo ^a   Chou, Jingyu ^a   Mine, Machiko ^a   Kuroboshi, Manabu ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; CARBOXYLIC ACIDS; DISPERSIONS; OXIDATION; SILICA GEL; SOLUTIONS;

COLUMN-FLOW SYSTEM; DISPERSE MEDIUM; REACTION CONDITIONS;

ALCOHOLS;

1 (4 METHOXYPHENYL) 1 ETHANONE; 1 INDANONE; 3 PHENYLPROPANOIC ACID; 4 METHYL 5 THIAZOLECARBOXALDEHYDE; 4 TERT BUTYLBENZALDEHYDE; 4 TERT BUTYLCYCLOHEXANONE; 4' TERT BUTYLACETOPHENONE; 6 UNDECANONE; ACETOPHENONE; ALDEHYDE DERIVATIVE; ANISALDEHYDE; BENZYLACETONE; CAMPHOR; CARBOXYLIC ACID DERIVATIVE; HYDROCINNAMALDEHYDE; HYPOCHLORITE SODIUM; KETONE DERIVATIVE; PHENYLACETIC ACID; SILICA GEL; UNCLASSIFIED DRUG; UNDECANOIC ACID; VERATRIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; OXIDATION;

EID: 4944235755     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.77.1745     Document Type: Article

References (143)

1. "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 7.
2. a) L. F. Fieser and M. Fieser, "Reagents for Organic Synthesis," Wiley, New York (1967), Vol. 1, pp. 142-147, 1059-1064.
3. b) G. I. Poos, G. E. Arth, R. E. Beyler, and L. H. Sarett, J. Am. Chem. Soc., 75, 422 (1953).
4. c) W. M. Coates and J. R. Corrigan, Chem. Ind. (London), 1969, 1594.
5. d) E. J. Corey and J. W. Suggs, Tetrahedron Lett., 16, 2647 (1975).
6. For a review, see: e) G. Piancatelli, A. Scettri, and M. D'Auria, Synthesis, 1982, 245.
7. For a review, see: A. J. Mancuso and D. Swern, Synthesis, 1981, 165.
8. a) D. B. Dess and J. C. Martin, J. Org. Chem., 48, 4155 (1983).
9. b) D. B. Dess and J. C. Martin, J. Am. Chem. Soc., 113, 7277 (1991).
10. a) M. Harfenist, A. Bavley, and W. A. Lazier, J. Org. Chem., 19, 1608 (1954).
11. b) M. Brink, Synthesis, 1975, 253.
12. For a review, see: c) A. J. Fatiadi, Synthesis, 1976, 65; 1976, 133.
13. For a review, see: c) A. J. Fatiadi, Synthesis, 1976, 65; 1976, 133.
14. a) L. M. Berkowitz and P. N. Rylander, J. Am. Chem. Soc., 80, 6682 (1958).
15. b) H. Tomioka, K. Takai, K. Oshima, and H. Nozaki, Tetrahedron Lett., 22, 1605 (1981).
16. D. H. R. Barton, J. P. Kitchin, D. J. Lester, W. B. Motherwell, and M. T. B. Papoula, Tetrahedron, Suppl., 37, 73 (1981).
17. A. M. Maione and A. Romeo, Synthesis, 1984, 955.
18. a) W. P. Griffith, S. V. Ley, G. P. Whitcombe, and A. D. White, J. Chem. Soc., Chem. Commun., 1987, 1625.
19. b) S. Giddings and A. Mills, J. Org. Chem., 53, 1103 (1988).
20. For a review, see: c) S. V. Ley, J. Norman, W. P. Griffith, and S. P. Marsden, Synthesis, 1994, 639. d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, and S. M. Brown, J. Am. Chem. Soc., 119, 12661 (1997).
21. For a review, see: c) S. V. Ley, J. Norman, W. P. Griffith, and S. P. Marsden, Synthesis, 1994, 639. d) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé-Regnaut, C. J. Urch, and S. M. Brown, J. Am. Chem. Soc., 119, 12661 (1997).
22. a) I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown, and C. J. Urch, Science, 274, 2044 (1996).
23. b) I. E. Markó, A. Gautier, I. Chellé-Regnaut, P. R. Giles, M. Tsukazaki, C. J. Urch, and S. M. Brown, J. Org. Chem., 63, 7576 (1998).
24. c) I. E. Markó, P. R. Giles, M. Tsukazaki, I. Chellé- Regnaut, A. Gautier, S. M. Brown, and C. J. Urch, J. Org. Chem., 64, 2433 (1999).
25. M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J. J. Grabowski, and P. J. Reider, Tetrahedron Lett., 39, 5323 (1998).
26. a) K. Sato, M. Aoki, J. Takagi, and R. Noyori, J. Am. Chem. Soc., 119, 12386 (1997).
27. b) K. Sato, M. Aoki, and R. Noyori, Science, 281, 1646 (1998).
28. a) T. Nishimura, T. Onoue, K. Ohe, and S. Uemura, Tetrahedron Lett, 39, 6011 (1998).
29. b) G.-J. ten Brink, I. W. C. E. Arends, and R. A. Sheldon, Science, 287, 1636 (2000).
30. c) G.-J. ten Brink, I. W. C. E. Arends, and R. A. Sheldon, Adv. Synth. Catal., 344, 355 (2002).
31. d) K. Mori, K. Yamaguchi, T. Hara, T. Mizugaki, K. Ebitani, and K. Kaneda, J. Am. Chem. Soc., 124, 11572 (2002).
32. e) Y. Uozumi and R. Nakao, Angew. Chem., Int. Ed., 42, 194 (2003).
33. f) S. K. Mandal, D. R. Jensen, J. S. Pugsley, and M. S. Sigman, J. Org. Chem., 68, 4600 (2003).
34. For reviews, see: a) J. M. Bobbitt and M. C. L. Flores, Heterocycles, 27, 509 (1988). b) A. E. J. de Nooy, A. C. Besemer, and H. van Bekkum, Synthesis, 1996, 1153.
35. For reviews, see: a) J. M. Bobbitt and M. C. L. Flores, Heterocycles, 27, 509 (1988). b) A. E. J. de Nooy, A. C. Besemer, and H. van Bekkum, Synthesis, 1996, 1153.
36. a) P. L. Anelli, C. Biffi, F. Montanari, and S. Quici, J. Org. Chem., 52, 2559 (1987).
37. b) P. L. Anelli, S. Banfi, F. Montanari, and S. Quici, J. Org. Chem., 54, 2970 (1989).
38. c) P. L. Anelli, F. Montanari, and S. Quici, Org. Synth., 69, 212 (1990).
39. a) B. Ganem, J. Org. Chem., 40, 1998 (1975).
40. b) J. A. Cella, J. A. Kelley, and E. F. Kenehan, J. Org. Chem., 40, 1860 (1975).
41. c) S. D. Rychnovsky and R. Vaidyanathan, J. Org. Chem., 64, 310 (1999).
42. T. Inokuchi, S. Matsumoto, T. Nishiyama, and S. Torii, J. Org. Chem., 55, 462 (1990).
43. a) M. Zhao, J. Li, E. Mano, Z. Song, D. M. Tschaen, E. J. J. Grabowski, and P. J. Reider, J. Org. Chem., 64, 2564 (1999).
44. b) J. E. Dettwiler and W. D. Lubell, J. Org. Chem., 68, 177 (2003).
45. F. Melvin, A. McNeill, P. J. F. Henderson, and R. B. Herbert, Tetrahedron Lett., 40, 1201 (1999).
46. C. Bolm, A. S. Magnus, and J. P. Hildebrand, Org. Lett., 2, 1173 (2000).
47. J. Einhorn, C. Einhorn, F. Ratajczak, and J.-L. Pierre, J. Org. Chem., 61, 7452 (1996).
48. a) A. De Mico, R. Margarita, L. Parlanti, A. Vescovi, and G. Piancatelli, J. Org. Chem., 62, 6974 (1997).
49. b) S. S. Kim and K. Nehru, Synlett, 2002, 616.
50. c) K. Sakuratani and H. Togo, Synthesis, 2003, 21.
51. a) L. De Luca, G. Giacomelli, and A. Porcheddu, Org. Lett., 3, 3041 (2001).
52. b) L. De Luca, G. Giacomelli, S. Masala, and A. Porcheddu, J. Org. Chem., 68, 4999 (2003).
53. a) M. F. Semmelhack, C. R. Schmid, D. A. Cortés, and C. S. Chou, J. Am. Chem. Soc., 106, 3374 (1984).
54. b) A. Dijksman, I. W. C. E. Arenas, and R. A. Sheldon, Chem. Commun., 1999, 1591.
55. c) A. Dijksman, A. Marino-González, A. M. i Payeras, I. W. C. E. Arends, and R. A. Sheldon, J. Am. Chem. Soc., 123, 6826 (2001).
56. d) I. A. Ansari and R. Gree, Org. Lett., 4, 1507 (2002).
57. W. A. Herrmann, J. P. Zoller, and R. W. Fischer, J. Organomet. Chem., 579, 404 (1999).
58. a) M. F. Semmelhack, C. S. Chou, and D. A. Cortés, J. Am. Chem. Soc., 105, 4492 (1983).
59. b) M. F. Semmelhack, C. R. Schmid, and D. A. Cortés, Tetrahedron Lett., 27, 1119 (1986).
60. c) T. Inokuchi, S. Matsumoto, and S. Torii, J. Org. Chem., 56, 2416 (1991).
61. d) Y. Kashiwagi, F. Kurashima, C. Kikuchi, J. Anzai, T. Osa, and J. M. Bobbitt, Chem. Commun., 1999, 1983.
62. e) Y. Kashiwagi, F. Kurashima, C. Kikuchi, J. Anzai, T. Osa, and J. M. Bobbitt, Tetrahedron Lett., 40, 6469 (1999).
63. f) K. Schnatbaum and H. J. Schäfer, Synthesis, 1999, 864.
64. a) R. Siedlecka, J. Skarżewski, and J. Młochowski, Tetrahedron Lett., 31, 2177 (1990).
65. b) M. R. Leanna, T. J. Sowin, and H. E. Morton, Tetrahedron Lett., 33, 5029 (1992).
66. c) C. Palomo, I. Ganboa, B. Odriozola, and A. Linden, Tetrahedron Lett., 38, 3093 (1997).
67. d) W. Adam, C. R. Sana-Möller, and P. A. Ganeshpure, Chem. Rev., 101, 3499 (2001).
68. e) M. Bouktaib, A. Atmani, and C. Rolando, Tetrahedron Lett., 43, 6263 (2002).
69. a) A. Dijksman, I. W. C. E. Arends, and R. A. Sheldon, Chem. Commun., 2000, 271.
70. b) T. Siu, S. Yekta, and A. K. Yudin, J. Am. Chem. Soc., 122, 11787 (2000).
71. c) C. Tanyeli and A. Gümüş, Tetrahedron Lett., 44, 1639 (2003).
72. M. J. Verhoef, J. A. Peters, and H. van Bekkum, Stud. Surf. Sci. Catal., 125, 465 (1999).
73. a) C. Bolm and T. Fey, Chem. Commun., 1999, 1795.
74. b) T. Fey, H. Fischer, S. Bachmann, K. Albert, and C. Bolm, J. Org. Chem., 66, 8154 (2001).
75. a) A. E. J. de Nooy, A. C. Besemer, and H. van Bekkum, Tetrahedron, 51, 8023 (1995).
76. b) A. Heeres, H. A. van Doren, K. F. Gotlieb, and I. P. Bleeker, Carbohydr. Res., 299, 221 (1997).
77. c) A. Medgyes, E. Farkas, A. Lipták, and V. Pozsgay, Tetrahedron, 53, 4159 (1997).
78. d) S. Lemoine, C. Thomazeau, D. Joannard, S. Trombotto, G. Descotes, A. Bouchu, and Y. Queneau, Carbohydr. Res., 326, 176 (2000).
79. e) P. L. Bragd, A. C. Besemer, and H. van Bekkum, Carbohydr. Res., 328, 355 (2000).
80. f) R. Ciriminna, J. Blum, D. Avnir, and M. Pagliaro, Chem. Commun., 2000, 1441.
81. g) R. Ciriminna and M. Pagliaro, Adv. Synth. Catal., 345, 383 (2003).
82. h) R. N. Desai and L. F. Blackwell, Synlett, 2003, 1981.
83. a) J. M. Bobbin, J. Org. Chem., 63, 9367 (1998).
84. b) C. A. Kernag, J. M. Bobbitt, and D. V. McGrath, Tetrahedron Lett., 40, 1635 (1999).
85. H. Tanaka, Y. Kawakami, K. Goto, and M. Kuroboshi, Tetrahedron Lett., 42, 445 (2001).
86. F. Montanari, M. Penso, S. Quici, and P. Viganò, J. Org. Chem., 50, 4888 (1985).
87. a) B. E. Douglas and D. H. McDaniel, "Concepts and Models of Inorganic Chemistry," Blaisdell, Massachusetts (1965), Chap. 7.6.
88. b) A. C. Besemer, A. E. J. de Nooy, and H. van Bekkum, 212th ACS National Meeting, Orlando, FL, Augest 25-29, 1996, Abstr., CELL-021.
89. a) C. R. Harington and R. C. G. Moggridge, J. Chem. Soc., 1939, 443.
90. b) R. L. White and I. D. Spenser, J. Am. Chem. Soc., 104, 4934 (1982).
91. c) T. Yokoyama, T. Setoyama, N. Fujita, and T. Maki, Stud. Surf. Sci. Catal., 90 (Acid-Base Catalysis II), 47 (1994).
92. d) M. Al Hariri, O. Galley, F. Pautet, and H. Fillion, Eur. J. Org. Chem., 1998, 593.
93. 4-Methyl-5-thiazolecarboxaldehyde (2m) is a useful intermediate for the synthesis of a potent cephalosporin family of antibiotics. a) K. Sakagami, K. Atsumi, A. Tamura, T. Yoshida, K. Nishihata, and S. Fukatsu, J. Antibiot., 43, 1047 (1990). b) Y. Okada, M. Sukegawa, T. Watanabe, H. Iwasawa, Y. Murai, and K. Iinuma, PCT Int. Appl., WO 98 58932 (1998); Chem. Abstr., 130, 81348x (1999). c) M. Kasai, S. Hatano, K. Nishimura, and N. Kakeya, PCT Int. Appl., WO 98 58933 (1998); Chem. Abstr., 130, 95424f (1999).
94. 4-Methyl-5-thiazolecarboxaldehyde (2m) is a useful intermediate for the synthesis of a potent cephalosporin family of antibiotics. a) K. Sakagami, K. Atsumi, A. Tamura, T. Yoshida, K. Nishihata, and S. Fukatsu, J. Antibiot., 43, 1047 (1990). b) Y. Okada, M. Sukegawa, T. Watanabe, H. Iwasawa, Y. Murai, and K. Iinuma, PCT Int. Appl., WO 98 58932 (1998); Chem. Abstr., 130, 81348x (1999). c) M. Kasai, S. Hatano, K. Nishimura, and N. Kakeya, PCT Int. Appl., WO 98 58933 (1998); Chem. Abstr., 130, 95424f (1999).
95. 4-Methyl-5-thiazolecarboxaldehyde (2m) is a useful intermediate for the synthesis of a potent cephalosporin family of antibiotics. a) K. Sakagami, K. Atsumi, A. Tamura, T. Yoshida, K. Nishihata, and S. Fukatsu, J. Antibiot., 43, 1047 (1990). b) Y. Okada, M. Sukegawa, T. Watanabe, H. Iwasawa, Y. Murai, and K. Iinuma, PCT Int. Appl., WO 98 58932 (1998); Chem. Abstr., 130, 81348x (1999). c) M. Kasai, S. Hatano, K. Nishimura, and N. Kakeya, PCT Int. Appl., WO 98 58933 (1998); Chem. Abstr., 130, 95424f (1999).
96. Estimated by elemental analysis: Found: C, 11.37; H, 1.86; N, 2.74%. Anal. Calcd for 0.64 mmol/g N-oxyl-immobilized silica gel 12: C, 11.53; H, 1.94; N, 2.69%.
97. Diols 1p-1r were prepared according to the manner of Sharpless AD reaction: K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, and X.-L. Zhang, J. Org. Chem., 57, 2768 (1992); Diol 1s was prepared according to the reference: W. E. Rosen, V. P. Toohey, and A. C. Shabica, J. Am. Chem. Soc., 80, 935 (1958).
98. Diols 1p-1r were prepared according to the manner of Sharpless AD reaction: K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, and X.-L. Zhang, J. Org. Chem., 57, 2768 (1992); Diol 1s was prepared according to the reference: W. E. Rosen, V. P. Toohey, and A. C. Shabica, J. Am. Chem. Soc., 80, 935 (1958).
99. For recent reviews on polymer-supported reagents and catalysts, see: a) S. J. Shuttleworth, S. M. Allin, and P. K. Sharma, Synthesis, 1997, 1217. b) S. J. Shuttleworth, S. M. Allin, R. D. Wilson, and D. Nasturica, Synthesis, 2000, 1035. c) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3815. d) G. Bhalay, A. Dunstan, and A. Glen, Synlett, 2000, 1846. e) A. Kirschning, H. Monenschein, and R. Wittenberg, Angew. Chem., Int. Ed., 40, 650 (2001). f) B. Clapham, T. S. Reger, and K. D. Janda, Tetrahedron, 57, 4637 (2001).
100. For recent reviews on polymer-supported reagents and catalysts, see: a) S. J. Shuttleworth, S. M. Allin, and P. K. Sharma, Synthesis, 1997, 1217. b) S. J. Shuttleworth, S. M. Allin, R. D. Wilson, and D. Nasturica, Synthesis, 2000, 1035. c) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3815. d) G. Bhalay, A. Dunstan, and A. Glen, Synlett, 2000, 1846. e) A. Kirschning, H. Monenschein, and R. Wittenberg, Angew. Chem., Int. Ed., 40, 650 (2001). f) B. Clapham, T. S. Reger, and K. D. Janda, Tetrahedron, 57, 4637 (2001).
101. For recent reviews on polymer-supported reagents and catalysts, see: a) S. J. Shuttleworth, S. M. Allin, and P. K. Sharma, Synthesis, 1997, 1217. b) S. J. Shuttleworth, S. M. Allin, R. D. Wilson, and D. Nasturica, Synthesis, 2000, 1035. c) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3815. d) G. Bhalay, A. Dunstan, and A. Glen, Synlett, 2000, 1846. e) A. Kirschning, H. Monenschein, and R. Wittenberg, Angew. Chem., Int. Ed., 40, 650 (2001). f) B. Clapham, T. S. Reger, and K. D. Janda, Tetrahedron, 57, 4637 (2001).
102. For recent reviews on polymer-supported reagents and catalysts, see: a) S. J. Shuttleworth, S. M. Allin, and P. K. Sharma, Synthesis, 1997, 1217. b) S. J. Shuttleworth, S. M. Allin, R. D. Wilson, and D. Nasturica, Synthesis, 2000, 1035. c) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3815. d) G. Bhalay, A. Dunstan, and A. Glen, Synlett, 2000, 1846. e) A. Kirschning, H. Monenschein, and R. Wittenberg, Angew. Chem., Int. Ed., 40, 650 (2001). f) B. Clapham, T. S. Reger, and K. D. Janda, Tetrahedron, 57, 4637 (2001).
103. For recent reviews on polymer-supported reagents and catalysts, see: a) S. J. Shuttleworth, S. M. Allin, and P. K. Sharma, Synthesis, 1997, 1217. b) S. J. Shuttleworth, S. M. Allin, R. D. Wilson, and D. Nasturica, Synthesis, 2000, 1035. c) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3815. d) G. Bhalay, A. Dunstan, and A. Glen, Synlett, 2000, 1846. e) A. Kirschning, H. Monenschein, and R. Wittenberg, Angew. Chem., Int. Ed., 40, 650 (2001). f) B. Clapham, T. S. Reger, and K. D. Janda, Tetrahedron, 57, 4637 (2001).
104. For recent reviews on polymer-supported reagents and catalysts, see: a) S. J. Shuttleworth, S. M. Allin, and P. K. Sharma, Synthesis, 1997, 1217. b) S. J. Shuttleworth, S. M. Allin, R. D. Wilson, and D. Nasturica, Synthesis, 2000, 1035. c) S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, and S. J. Taylor, J. Chem. Soc., Perkin Trans. 1, 2000, 3815. d) G. Bhalay, A. Dunstan, and A. Glen, Synlett, 2000, 1846. e) A. Kirschning, H. Monenschein, and R. Wittenberg, Angew. Chem., Int. Ed., 40, 650 (2001). f) B. Clapham, T. S. Reger, and K. D. Janda, Tetrahedron, 57, 4637 (2001).
105. a) S. Itsuno, K. Ito, T. Maruyama, N. Kanda, A. Hirao, and S. Nakahama, Bull. Chem. Soc. Jpn., 59, 3329 (1986).
106. b) K. Kamahori, K. Ito, and S. Itsuno, J. Org. Chem., 61, 8321 (1996).
107. c) D. A. Annis and E. N. Jacobsen, J. Am. Chem. Soc., 121, 4147 (1999).
108. d) A. M. Hafez, A. E. Taggi, H. Wack, W. J. Drury, III, and T. Lectka, Org. Lett., 2, 3963 (2000).
109. e) A. M. Hafez, A. E. Taggi, T. Dudding, and T. Lectka, J. Am. Chem. Soc., 123, 10853 (2001).
110. f) K. Ishihara, A. Hasegawa, and H. Yamamoto, Synlett, 2002, 1296.
111. a) G. P. Ponzano, PCT Int. Appl., WO 2001081656 (2001); Chem. Abstr., 135, 324334z (2001).
112. b) G. E. Itkin, Russ., RU 2153540 (2000); Chem. Abstr., 136, 44581w (2002).
113. c) V. V. Bannikov, Russ., RU 2162489 (2001); Chem. Abstr., 136, 157833y (2002).
114. d) V. Zolotarsky, I. A. Ivanter, and M. J. Geusic, PCT Int. Appl., WO 2002061182 (2002); Chem. Abstr., 137, 146915w (2002).
115. e) K. Yokota, M. Matsushima, J. Morita, and K. Okano, Jpn. Kokai Tokkyo Koho, JP 2002068388 (2002); Chem. Abstr., 136, 202205h (2002).
116. S. Cacchi, G. Fabrizi, F. Gavazza, and A. Goggiamani, Org. Lett., 5, 289 (2003).
117. H. B. Kwon, B. H. McKee, and J. K. Stille, J. Org. Chem., 55, 3114 (1990).
118. Y. Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T. Iwahama, and T. Nishiyama, J. Org. Chem., 60, 3934 (1995).
119. P. Ceccherelli, M. Curini, M. C. Marcotullio, and O. Rosati, J. Org. Chem., 55, 311 (1990).
120. K. Sakai, N. Hida, and K. Kondo, Bull. Chem. Soc. Jpn., 59, 179 (1986).
121. E. M. Brown, F. H. Fuller, S. C. Hebert, and J. E. Garrett, Jr., U. S. Patent US 5688938 (1997); Chem. Abstr., 128, 30379j (1998).
122. R. G. Syvret, T. P. Nguyen, V. L. Bulleck, and R. D. Rieth, Eur. Pat. Appl., EP 1138657 A1 (2001); Chem. Abstr., 135, 272548a (2001).
123. J. Louie, C. W. Bielawski, and R. H. Grubbs, J. Am. Chem. Soc., 123, 11312 (2001).
124. A. Arase, M. Hoshi, and Y. Masuda, Bull. Chem. Soc. Jpn., 57, 209 (1984).
125. S. Torii, T. Inokuchi, and T. Sugiura, J. Org. Chem., 51, 155 (1986).
126. W. L. Meyer, C. E. Capshew, J. H. Johnson, A. R. Klusener, A. P. Lobo, and R. N. McCarty, J. Org. Chem., 42, 527 (1977).
127. S. S. Chaudhari and K. G. Akamanchi, Synthesis, 1999, 760.
128. G. Y. Han, P. F. Han, J. Perkins, and H. C. McBay, J. Org. Chem., 46, 4695 (1981).
129. T. Suzuki, K. Morita, M. Tsuchida, and K. Hiroi, J. Org. Chem., 68, 1601 (2003).
130. M. Shi and Y.-S. Feng, J. Org. Chem., 66, 3235 (2001).
131. P. Haake and L. P. Bausher, J. Phys. Chem., 72, 2213 (1968).
132. J. J. D'Amico and T. W. Bartram, J. Org. Chem., 25, 1336 (1960).
133. M. Fujii, K. Nakamura, S. Yasui, S. Oka, and A. Ohno, Bull. Chem. Soc. Jpn., 60, 2423 (1987).
134. M. Kawashima, T. Sato, and T. Fujisawa, Tetrahedron, 45, 403 (1989).
135. V. B. Helavi, S. B. Solabannavar, U. V. Desai, and R. B. Mane, J. Chem. Res., Symop., 2003, 174.
136. J. Blum and B. Zinger, J. Org. Chem., 43, 2961 (1978).
137. T. P. Burns and R. D. Rieke, J. Org. Chem., 52, 3674 (1987).
138. H.-R. Bjørsvik, L. Liguori, and J. A. V. Merinero, J. Org. Chem., 67, 7493 (2002).
139. P. K. Kachroo, T. K. Razdan, M. A. Qurishi, M. A. Khuroo, S. Koul, and K. L. Dhar, Phytochemistry, 29, 1014 (1990).
140. A. Silveira, Jr. and S. K. Satra, J. Org. Chem., 44, 873 (1979).
141. Y. Ishii, T. Yoshida, K. Yamawaki, and M. Ogawa, J. Org. Chem., 53, 5549 (1988).
142. H. C. Brown, S. C. Kim, and S. Krishnamurthy, J. Org. Chem., 45, 1 (1980).
143. M. T. Nuñez and V. S. Martín, J. Org. Chem., 55, 1928 (1990).