Reductive dehalogenation of aliphatic vic-dihalides with metallic samarium in a methanolic medium

Tetrahedron Letters

Volumn 37, Issue 52, 1996, Pages 9313-9316

  Yanada, Reiko ^a   Negoro, Nobuyuki ^a   Yanada, Kazuo ^b   Fujita, Tetsuro ^b  

^a KYOTO UNIVERSITY   (Japan)

^b SETSUNAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE;

ARTICLE; DEBROMINATION; DEHALOGENATION; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030599660     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)82951-6     Document Type: Article

References (34)

1. 1. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986, 42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
2. 1. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986, 42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
3. 1. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986, 42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
4. 1. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986, 42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
5. 1. Kagan, H. B.; Namy, J. L. Tetrahedron, 1986, 42, 6573-6614. Kagan, H. B. Nouv. J. Chim., 1990, 14, 453-460. Molander, G. A. Chem. Rev., 1992, 92, 29-68. Molander, G. A. Organic Reactions, 1994, 46, 211-367. Molander, G. A.; Harris, C. R. Chem. Rev., 1996, 96, 307-338.
6. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
7. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
8. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
9. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
10. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
11. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
12. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
13. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
14. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
15. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
16. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
17. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
18. 2. Molander, G. A.; Etter, J. B. Tetraheron Lett., 1984, 25, 3281-3284. Imamoto, T.; Takeyama, T.; Koto, H. Tetraheron Lett., 1986, 27, 3243-3246. Fukuzawa, S.; Fujinami, T.; Sakai, S. J. Chem. Soc., Chem. Commum., 1986, 475-476. Molander, G. A.; Etter, J. B. J. Org. Chem., 1986, 51, 1778-1786. Hou, Z.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 3118-3120. Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Org. Chem., 1988, 53, 6077-6084. Imamoto, T.; Kamiya, Y.; Hatajima, T.; Takahashi, H. Tetrahedron Lett., 1989, 30, 5149-5152. Yamazaki, T.; Lin, J. T.; Takeda, M.; Kitazume, T. Tetrahedron; Asymmetry, 1990, 1, 351-354. Ogawa, A.; Nanke, T.; Takami, N.; Sumino, Y.; Ryu, I.; Sonoda, N. Chem. Let., 1994, 379-380. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1994, 42, 402-404. Taniguchi, Y.; Fujii, N.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem., 1995, 491, 173-179. Kamochi, Y.; Kudo, T. Chem. Pharm. Bull., 1995, 43, 1422-1424. Lautens, M.; Delanghe, P. H. M. J. Org. Chem., 1995, 60, 2474-2487.
19. 3. Yanada, R.; Bessho, K.; Yanada, K. Synlett, 1995, 443-444.
20. 2 in methanol. Yanada, R.; Negoro, N.; Bessho, K.; Yanada, K. Synlett, 1995, 1261-1263.
21. 5. For example: Fukunaga, K.; Yamaguchi, H. Synthesis, 1981, 879-880. Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem., 1982, 47, 876-879. Nakayama, J.; Machida, H.; Hoshino, M. Tetrahedron Lett., 1983, 24, 3001-3004. Landini, D.; Milesi, L.; Quadri, M. L.; Rolla, F. J. Org. Chem., 1984, 49, 152-153. Davies, S. G.; Thomas, S. E. Synthesis, 1984, 1027-1029. Yanada, K.; Yanada, R.; Meguri, H. J. Chem. Soc., Chem. Commum., 1990, 730-732. Khurana, J. M.; Maikap, G. C.; Sahoo, P. K. Synthesis, 1991, 827-828.
22. 5. For example: Fukunaga, K.; Yamaguchi, H. Synthesis, 1981, 879-880. Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem., 1982, 47, 876-879. Nakayama, J.; Machida, H.; Hoshino, M. Tetrahedron Lett., 1983, 24, 3001-3004. Landini, D.; Milesi, L.; Quadri, M. L.; Rolla, F. J. Org. Chem., 1984, 49, 152-153. Davies, S. G.; Thomas, S. E. Synthesis, 1984, 1027-1029. Yanada, K.; Yanada, R.; Meguri, H. J. Chem. Soc., Chem. Commum., 1990, 730-732. Khurana, J. M.; Maikap, G. C.; Sahoo, P. K. Synthesis, 1991, 827-828.
23. 5. For example: Fukunaga, K.; Yamaguchi, H. Synthesis, 1981, 879-880. Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem., 1982, 47, 876-879. Nakayama, J.; Machida, H.; Hoshino, M. Tetrahedron Lett., 1983, 24, 3001-3004. Landini, D.; Milesi, L.; Quadri, M. L.; Rolla, F. J. Org. Chem., 1984, 49, 152-153. Davies, S. G.; Thomas, S. E. Synthesis, 1984, 1027-1029. Yanada, K.; Yanada, R.; Meguri, H. J. Chem. Soc., Chem. Commum., 1990, 730-732. Khurana, J. M.; Maikap, G. C.; Sahoo, P. K. Synthesis, 1991, 827-828.
24. 5. For example: Fukunaga, K.; Yamaguchi, H. Synthesis, 1981, 879-880. Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem., 1982, 47, 876-879. Nakayama, J.; Machida, H.; Hoshino, M. Tetrahedron Lett., 1983, 24, 3001-3004. Landini, D.; Milesi, L.; Quadri, M. L.; Rolla, F. J. Org. Chem., 1984, 49, 152-153. Davies, S. G.; Thomas, S. E. Synthesis, 1984, 1027-1029. Yanada, K.; Yanada, R.; Meguri, H. J. Chem. Soc., Chem. Commum., 1990, 730-732. Khurana, J. M.; Maikap, G. C.; Sahoo, P. K. Synthesis, 1991, 827-828.
25. 5. For example: Fukunaga, K.; Yamaguchi, H. Synthesis, 1981, 879-880. Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem., 1982, 47, 876-879. Nakayama, J.; Machida, H.; Hoshino, M. Tetrahedron Lett., 1983, 24, 3001-3004. Landini, D.; Milesi, L.; Quadri, M. L.; Rolla, F. J. Org. Chem., 1984, 49, 152-153. Davies, S. G.; Thomas, S. E. Synthesis, 1984, 1027-1029. Yanada, K.; Yanada, R.; Meguri, H. J. Chem. Soc., Chem. Commum., 1990, 730-732. Khurana, J. M.; Maikap, G. C.; Sahoo, P. K. Synthesis, 1991, 827-828.
26. 5. For example: Fukunaga, K.; Yamaguchi, H. Synthesis, 1981, 879-880. Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem., 1982, 47, 876-879. Nakayama, J.; Machida, H.; Hoshino, M. Tetrahedron Lett., 1983, 24, 3001-3004. Landini, D.; Milesi, L.; Quadri, M. L.; Rolla, F. J. Org. Chem., 1984, 49, 152-153. Davies, S. G.; Thomas, S. E. Synthesis, 1984, 1027-1029. Yanada, K.; Yanada, R.; Meguri, H. J. Chem. Soc., Chem. Commum., 1990, 730-732. Khurana, J. M.; Maikap, G. C.; Sahoo, P. K. Synthesis, 1991, 827-828.
27. 5. For example: Fukunaga, K.; Yamaguchi, H. Synthesis, 1981, 879-880. Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem., 1982, 47, 876-879. Nakayama, J.; Machida, H.; Hoshino, M. Tetrahedron Lett., 1983, 24, 3001-3004. Landini, D.; Milesi, L.; Quadri, M. L.; Rolla, F. J. Org. Chem., 1984, 49, 152-153. Davies, S. G.; Thomas, S. E. Synthesis, 1984, 1027-1029. Yanada, K.; Yanada, R.; Meguri, H. J. Chem. Soc., Chem. Commum., 1990, 730-732. Khurana, J. M.; Maikap, G. C.; Sahoo, P. K. Synthesis, 1991, 827-828.
28. 6. Yanada, R.; Bessho, K.; Yanada, K. Chem. Lett., 1994, 1279-1282.
29. 7. It was reported that water accelerated the reductions of alkyl and aryl iodides. Hasegawa, E.; Curran, D. P. J. Org. Chem., 1993, 58, 5008-5010.
30. 2 because the ligand exchange reaction may occur in methanol. Namy, J. L.; Girard, P.; Kagan, H. B.; Caro, P. E. Nouv. J. Chim., 1981, 5, 479-484.
31. 9. Because bromination proceeds by trans addition mechanism (dl from cis and meso from trans), the ratio of dl-and meso-1,2-dibromocyclododecane may be 2.3:1 the same as that of the starting cyclododecene, but such ratios could not be elucidated. The debromination product was a mixture of cis-and frans-dodecene (1.4:1). The increase in the trans-dodecene ratio suggests that a part of dl-1,2-dibromododecane gives trans-dodecene via a radical or anion intermediate.
32. 10. Inanaga, J.; Sakai, S.; Handa, Y.; Yamaguchi, M.; Yokoyama, Y. Chem. Lett., 1991, 2117-2118.
33. 11. Inanaga, J.; Handa, Y.; Tabuchi, T.; Takanosi, T.; Otsubo, K.; Yamaguchi, M.; Hanamoto, T. Tetrahedron Lett., 1991, 32, 6557-6558.
34. 12. Cabrera, A.; Alper, H. Tetrahedron Lett., 1992, 33, 5007-5008.