Activation of C-O and C-N Bonds in Allylic Alcohols and Amines by Palladium Complexes Promoted by CO2. Synthetic Applications to Allylation of Nucleophiles, Carbonylation, and Allylamine Disproportionation

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 4, 1996, Pages 1065-1078

  Sakamoto, Masato ^a   Shimizu, Isao ^a   Yamamoto, Akio ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000475514     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1065     Document Type: Article

References (79)

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20. For examples of previous studies concerning the C-O bond cleavage of allylic alcohols by transition metal complexes, see: a) G. W. Parshall, Z. Naturforsch. B, 18B, 772 (1963); b) J. K. Nicholson and B. L. Shaw, Proc. Chem. Soc., 1963, 282; c) T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto, J. Organomet. Chem., 5, 3559 (1986); d) Y. Yang and M. H. Chisholm, Polyhedron, 11, 2813 (1992); e) S. Jang, L. M. Atagi, and J. M. Mayer, J. Am. Chem. Soc., 112, 6413 (1990); f) M. Moreno-Mañas and A. Trius, Tetrahedron Lett., 22, 3109 (1981); g) G. Consiglio, O. Piccolo, L. Roncetti, and F. Morandini, Tetrahedron, 42, 2043 (1986); h) C. Chuit, H. Felkin, C. Frajerman, G. Roussi, and G. Swierczewski, J. Organomet. Chem., 127, 371 (1977); i) H. Felkin, E. Jampel-Costa, and G. Swierczewski, J. Organomet. Chem., 134, 265 (1977).
21. For examples of previous studies concerning the C-O bond cleavage of allylic alcohols by transition metal complexes, see: a) G. W. Parshall, Z. Naturforsch. B, 18B, 772 (1963); b) J. K. Nicholson and B. L. Shaw, Proc. Chem. Soc., 1963, 282; c) T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto, J. Organomet. Chem., 5, 3559 (1986); d) Y. Yang and M. H. Chisholm, Polyhedron, 11, 2813 (1992); e) S. Jang, L. M. Atagi, and J. M. Mayer, J. Am. Chem. Soc., 112, 6413 (1990); f) M. Moreno-Mañas and A. Trius, Tetrahedron Lett., 22, 3109 (1981); g) G. Consiglio, O. Piccolo, L. Roncetti, and F. Morandini, Tetrahedron, 42, 2043 (1986); h) C. Chuit, H. Felkin, C. Frajerman, G. Roussi, and G. Swierczewski, J. Organomet. Chem., 127, 371 (1977); i) H. Felkin, E. Jampel-Costa, and G. Swierczewski, J. Organomet. Chem., 134, 265 (1977).
22. For examples of previous studies concerning the C-O bond cleavage of allylic alcohols by transition metal complexes, see: a) G. W. Parshall, Z. Naturforsch. B, 18B, 772 (1963); b) J. K. Nicholson and B. L. Shaw, Proc. Chem. Soc., 1963, 282; c) T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto, J. Organomet. Chem., 5, 3559 (1986); d) Y. Yang and M. H. Chisholm, Polyhedron, 11, 2813 (1992); e) S. Jang, L. M. Atagi, and J. M. Mayer, J. Am. Chem. Soc., 112, 6413 (1990); f) M. Moreno-Mañas and A. Trius, Tetrahedron Lett., 22, 3109 (1981); g) G. Consiglio, O. Piccolo, L. Roncetti, and F. Morandini, Tetrahedron, 42, 2043 (1986); h) C. Chuit, H. Felkin, C. Frajerman, G. Roussi, and G. Swierczewski, J. Organomet. Chem., 127, 371 (1977); i) H. Felkin, E. Jampel-Costa, and G. Swierczewski, J. Organomet. Chem., 134, 265 (1977).
23. For examples of previous studies concerning the C-O bond cleavage of allylic alcohols by transition metal complexes, see: a) G. W. Parshall, Z. Naturforsch. B, 18B, 772 (1963); b) J. K. Nicholson and B. L. Shaw, Proc. Chem. Soc., 1963, 282; c) T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto, J. Organomet. Chem., 5, 3559 (1986); d) Y. Yang and M. H. Chisholm, Polyhedron, 11, 2813 (1992); e) S. Jang, L. M. Atagi, and J. M. Mayer, J. Am. Chem. Soc., 112, 6413 (1990); f) M. Moreno-Mañas and A. Trius, Tetrahedron Lett., 22, 3109 (1981); g) G. Consiglio, O. Piccolo, L. Roncetti, and F. Morandini, Tetrahedron, 42, 2043 (1986); h) C. Chuit, H. Felkin, C. Frajerman, G. Roussi, and G. Swierczewski, J. Organomet. Chem., 127, 371 (1977); i) H. Felkin, E. Jampel-Costa, and G. Swierczewski, J. Organomet. Chem., 134, 265 (1977).
24. For examples of previous studies concerning the C-O bond cleavage of allylic alcohols by transition metal complexes, see: a) G. W. Parshall, Z. Naturforsch. B, 18B, 772 (1963); b) J. K. Nicholson and B. L. Shaw, Proc. Chem. Soc., 1963, 282; c) T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto, J. Organomet. Chem., 5, 3559 (1986); d) Y. Yang and M. H. Chisholm, Polyhedron, 11, 2813 (1992); e) S. Jang, L. M. Atagi, and J. M. Mayer, J. Am. Chem. Soc., 112, 6413 (1990); f) M. Moreno-Mañas and A. Trius, Tetrahedron Lett., 22, 3109 (1981); g) G. Consiglio, O. Piccolo, L. Roncetti, and F. Morandini, Tetrahedron, 42, 2043 (1986); h) C. Chuit, H. Felkin, C. Frajerman, G. Roussi, and G. Swierczewski, J. Organomet. Chem., 127, 371 (1977); i) H. Felkin, E. Jampel-Costa, and G. Swierczewski, J. Organomet. Chem., 134, 265 (1977).
25. For examples of previous studies concerning the C-O bond cleavage of allylic alcohols by transition metal complexes, see: a) G. W. Parshall, Z. Naturforsch. B, 18B, 772 (1963); b) J. K. Nicholson and B. L. Shaw, Proc. Chem. Soc., 1963, 282; c) T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto, J. Organomet. Chem., 5, 3559 (1986); d) Y. Yang and M. H. Chisholm, Polyhedron, 11, 2813 (1992); e) S. Jang, L. M. Atagi, and J. M. Mayer, J. Am. Chem. Soc., 112, 6413 (1990); f) M. Moreno-Mañas and A. Trius, Tetrahedron Lett., 22, 3109 (1981); g) G. Consiglio, O. Piccolo, L. Roncetti, and F. Morandini, Tetrahedron, 42, 2043 (1986); h) C. Chuit, H. Felkin, C. Frajerman, G. Roussi, and G. Swierczewski, J. Organomet. Chem., 127, 371 (1977); i) H. Felkin, E. Jampel-Costa, and G. Swierczewski, J. Organomet. Chem., 134, 265 (1977).
26. For examples of previous studies concerning the C-O bond cleavage of allylic alcohols by transition metal complexes, see: a) G. W. Parshall, Z. Naturforsch. B, 18B, 772 (1963); b) J. K. Nicholson and B. L. Shaw, Proc. Chem. Soc., 1963, 282; c) T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto, J. Organomet. Chem., 5, 3559 (1986); d) Y. Yang and M. H. Chisholm, Polyhedron, 11, 2813 (1992); e) S. Jang, L. M. Atagi, and J. M. Mayer, J. Am. Chem. Soc., 112, 6413 (1990); f) M. Moreno-Mañas and A. Trius, Tetrahedron Lett., 22, 3109 (1981); g) G. Consiglio, O. Piccolo, L. Roncetti, and F. Morandini, Tetrahedron, 42, 2043 (1986); h) C. Chuit, H. Felkin, C. Frajerman, G. Roussi, and G. Swierczewski, J. Organomet. Chem., 127, 371 (1977); i) H. Felkin, E. Jampel-Costa, and G. Swierczewski, J. Organomet. Chem., 134, 265 (1977).
27. For examples of previous studies concerning the C-O bond cleavage of allylic alcohols by transition metal complexes, see: a) G. W. Parshall, Z. Naturforsch. B, 18B, 772 (1963); b) J. K. Nicholson and B. L. Shaw, Proc. Chem. Soc., 1963, 282; c) T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto, J. Organomet. Chem., 5, 3559 (1986); d) Y. Yang and M. H. Chisholm, Polyhedron, 11, 2813 (1992); e) S. Jang, L. M. Atagi, and J. M. Mayer, J. Am. Chem. Soc., 112, 6413 (1990); f) M. Moreno-Mañas and A. Trius, Tetrahedron Lett., 22, 3109 (1981); g) G. Consiglio, O. Piccolo, L. Roncetti, and F. Morandini, Tetrahedron, 42, 2043 (1986); h) C. Chuit, H. Felkin, C. Frajerman, G. Roussi, and G. Swierczewski, J. Organomet. Chem., 127, 371 (1977); i) H. Felkin, E. Jampel-Costa, and G. Swierczewski, J. Organomet. Chem., 134, 265 (1977).
28. For examples of previous studies concerning the C-O bond cleavage of allylic alcohols by transition metal complexes, see: a) G. W. Parshall, Z. Naturforsch. B, 18B, 772 (1963); b) J. K. Nicholson and B. L. Shaw, Proc. Chem. Soc., 1963, 282; c) T. Yamamoto, M. Akimoto, O. Saito, and A. Yamamoto, J. Organomet. Chem., 5, 3559 (1986); d) Y. Yang and M. H. Chisholm, Polyhedron, 11, 2813 (1992); e) S. Jang, L. M. Atagi, and J. M. Mayer, J. Am. Chem. Soc., 112, 6413 (1990); f) M. Moreno-Mañas and A. Trius, Tetrahedron Lett., 22, 3109 (1981); g) G. Consiglio, O. Piccolo, L. Roncetti, and F. Morandini, Tetrahedron, 42, 2043 (1986); h) C. Chuit, H. Felkin, C. Frajerman, G. Roussi, and G. Swierczewski, J. Organomet. Chem., 127, 371 (1977); i) H. Felkin, E. Jampel-Costa, and G. Swierczewski, J. Organomet. Chem., 134, 265 (1977).
29. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
30. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
31. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
32. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
33. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
34. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
35. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
36. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
37. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
38. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
39. 2 is observed, see: a) Y. Inoue, K. Ohuchi, I. Yen, and S. Imaizumi, Bull. Chem. Soc. Jpn., 62, 3518 (1989); b) K. E. Atkins, W. E. Walker, and R. M. Manyik, J. Chem. Soc., Chem. Commun., 1971, 330; c) Y. Sasaki, Y. Inoue, and H. Hashimoto, J. Chem. Soc., Chem. Commun., 1976, 605; d) Y. Inoue, Y. Sasaki, and H. Hashimoto,Bull. Chem. Soc. Jpn., 51, 2375 (1978); e) Y. Tokitoh, Japanese Patent, Kokai, H4-208233 (1992); f) F. Bergamini, F. Panella, R. Santi, and E. Antonelli, J. Chem. Soc., Chem. Commun., 1995, 931; g) K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, and S. Teranishi, J. Org. Chem., 46, 2356 (1981); h) J.-P. Bianchini, B. Waegell, E. M. Gaydou, H. Rzehak, and W. Keim, J. Mol. Catal., 10, 247 (1981); i) A. Musco, J. Mol. Catal., 1, 443 (1976); j) A. Musco and A. Silvani, J. Organomet. Chem., 88, C41 (1975); k) J. F. Kohnle, L. H. Slaugh, and K. L. Nakamaye, J. Am. Chem. Soc., 91, 5904 (1969).
40. a) K. E. Atkins, W. E. Walker, and R. M. Manyik, Tetrahedron Lett., 43, 3821 (1970);
41. b) Y. Ishimura and N. Nagato, Japanese Patent, Kokai, S63-2958 (1988);
42. c) Y. Ishimura, T. Oe, Y. Suyama, and N. Nagato, U. S. Patent 4942262 (1990);
43. d) J. Fumkawa, J. Kiji, K. Yamamoto, and T. Tojo, Tetrahedron, 29, 3149 (1973);
44. e) S. Murahashi, T. Shimamura, and I. Moritani, J. Chem. Soc., Chem. Commun., 1974, 931.
45. W. D. McGhee, D. P. Riley, M. E. Christ, and K. M. Christ, Organometallics, 12, 1429 (1993).
46. a) D. E. Bergbreiter and D. A. Weatherford, J. Chem. Soc., Chem. Commun., 1989, 883;
47. b) D. E. Bergbreiter and D. A. Weatherford, J. Org. Chem., 54, 2726 (1989);
48. c) see Ref. 12 (a).
49. T. Yamamoto, J. Ishizu, and A. Yamamoto, Bull. Chem. Soc. Jpn., 55, 623 (1982).
50. I. Shimizu, T. Yamada, and J. Tsuji, Tetrahedron Lett., 21, 3199 (1980);
51. b) T. Tsuda, Y. Chujo, S. Nishi, K. Tawara, and T. Saegusa, J. Am. Chem. Soc., 102, 6381 (1980).
52. J. Tsuji, J. Kiji, S. Imamura, and M. Morikawa, J. Am. Chem. Soc., 86, 4350 (1964).
53. a) J. Tsuji, K. Sato, and H. Okumoto, Tetrahedron Lett., 23, 5189 (1982);
54. b) J. Tsuji, K. Sato, and H. Okumoto, J. Org. Chem., 49, 1341 (1984).
55. For some examples of direct carbonylation of allylic alcohols involving C-O bond cleavage: a) D. Medema, R. van Helden, and C. F. Kohll, Inorg. Chim. Acta, 1969, 255; b) J. F. Knifton, J. Organomet.Chem., 188, 223 (1980); c) I. Amer and H. Alper, J. Mol. Catal., 54, L33 (1989); d) W. Himmerle, W. Hoffmann, and L. Janitschke, Japanese Patent, Kokai, S60-152437 (1985).
56. For some examples of direct carbonylation of allylic alcohols involving C-O bond cleavage: a) D. Medema, R. van Helden, and C. F. Kohll, Inorg. Chim. Acta, 1969, 255; b) J. F. Knifton, J. Organomet.Chem., 188, 223 (1980); c) I. Amer and H. Alper, J. Mol. Catal., 54, L33 (1989); d) W. Himmerle, W. Hoffmann, and L. Janitschke, Japanese Patent, Kokai, S60-152437 (1985).
57. For some examples of direct carbonylation of allylic alcohols involving C-O bond cleavage: a) D. Medema, R. van Helden, and C. F. Kohll, Inorg. Chim. Acta, 1969, 255; b) J. F. Knifton, J. Organomet.Chem., 188, 223 (1980); c) I. Amer and H. Alper, J. Mol. Catal., 54, L33 (1989); d) W. Himmerle, W. Hoffmann, and L. Janitschke, Japanese Patent, Kokai, S60-152437 (1985).
58. For some examples of direct carbonylation of allylic alcohols involving C-O bond cleavage: a) D. Medema, R. van Helden, and C. F. Kohll, Inorg. Chim. Acta, 1969, 255; b) J. F. Knifton, J. Organomet.Chem., 188, 223 (1980); c) I. Amer and H. Alper, J. Mol. Catal., 54, L33 (1989); d) W. Himmerle, W. Hoffmann, and L. Janitschke, Japanese Patent, Kokai, S60-152437 (1985).
59. a) S. Murahashi, Y. Imada, and K. Nishimura, Tetrahedron, 50, 453 (1994);
60. b) S. Murahashi, Y. Imada, and K. Nishimura, J. Chem. Soc., Chem. Commun., 1988, 1578.
61. R. S. Srivastava, G. Singh, M. Nakano, K. Osakada, F. Ozawa, and A. Yamamoto, J. Organomet. Chem., 451, 221 (1993).
62. F. Ozawa, T. Son, S. Ebina, K. Osakada, and A. Yamamoto, Organometallics, 11, 171 (1992).
63. F. Ozawa, T. Son, K. Osakada, and A. Yamamoto, J. Chem. Soc., Chem. Commun., 1989, 1067.
64. 2 on disproportionation of diallylamine is the effect of the acidic character of diallylcarbamic acid 30 formed in Eq. 7. The proton in 30 may interact with diallylamine to form an ammonium salt that may promote the N-allyl bond cleavage; for example see: a) B. M. Trost and E. Keinan, J. Org. Chem., 45, 2741 (1980); b) A. J. Chalk, V. Wertheimer, and S. A. Magennis, J. Mol. Catal., 19, 189 (1983); c) S. Murahashi, Y. Makabe, and K. Kunita., J. Org. Chem., 53, 4489 (1988); d) F. Garro-Helion, A. Merzouk, and F. Guibé, J. Org. Chem., 58, 6109 (1993).
65. 2 on disproportionation of diallylamine is the effect of the acidic character of diallylcarbamic acid 30 formed in Eq. 7. The proton in 30 may interact with diallylamine to form an ammonium salt that may promote the N-allyl bond cleavage; for example see: a) B. M. Trost and E. Keinan, J. Org. Chem., 45, 2741 (1980); b) A. J. Chalk, V. Wertheimer, and S. A. Magennis, J. Mol. Catal., 19, 189 (1983); c) S. Murahashi, Y. Makabe, and K. Kunita., J. Org. Chem., 53, 4489 (1988); d) F. Garro-Helion, A. Merzouk, and F. Guibé, J. Org. Chem., 58, 6109 (1993).
66. 2 on disproportionation of diallylamine is the effect of the acidic character of diallylcarbamic acid 30 formed in Eq. 7. The proton in 30 may interact with diallylamine to form an ammonium salt that may promote the N-allyl bond cleavage; for example see: a) B. M. Trost and E. Keinan, J. Org. Chem., 45, 2741 (1980); b) A. J. Chalk, V. Wertheimer, and S. A. Magennis, J. Mol. Catal., 19, 189 (1983); c) S. Murahashi, Y. Makabe, and K. Kunita., J. Org. Chem., 53, 4489 (1988); d) F. Garro-Helion, A. Merzouk, and F. Guibé, J. Org. Chem., 58, 6109 (1993).
67. 2 on disproportionation of diallylamine is the effect of the acidic character of diallylcarbamic acid 30 formed in Eq. 7. The proton in 30 may interact with diallylamine to form an ammonium salt that may promote the N-allyl bond cleavage; for example see: a) B. M. Trost and E. Keinan, J. Org. Chem., 45, 2741 (1980); b) A. J. Chalk, V. Wertheimer, and S. A. Magennis, J. Mol. Catal., 19, 189 (1983); c) S. Murahashi, Y. Makabe, and K. Kunita., J. Org. Chem., 53, 4489 (1988); d) F. Garro-Helion, A. Merzouk, and F. Guibé, J. Org. Chem., 58, 6109 (1993).
68. J. R. Dogle, P. E. Slade, and H. B. Jonassen, Inorg. Synth., 6, 218 (1960).
69. T. Ukai, H. Kawazura, Y. Ishii, J. J. Bonnet, and J. A. Ibers, J. Organomet. Chem., 65, 253 (1974).
70. 2 and related complexes, see: a) M. C. Mazza and C. G. Pierpont, Inorg. Chem., 12, 2955 (1973); b) C. G. Pierpont and M. C. Mazza, Inorg. Chem., 13, 1891 (1974); c) F. Paul, J. Patt, and J. F. Hartwig, Organometallics, 14, 3030 (1995); d) M. Moreno-Mañas, F. Pajuelo, and R. Pleixats, J. Org. Chem., 60, 2396 (1995), see also references cited therein.
71. 2 and related complexes, see: a) M. C. Mazza and C. G. Pierpont, Inorg. Chem., 12, 2955 (1973); b) C. G. Pierpont and M. C. Mazza, Inorg. Chem., 13, 1891 (1974); c) F. Paul, J. Patt, and J. F. Hartwig, Organometallics, 14, 3030 (1995); d) M. Moreno-Mañas, F. Pajuelo, and R. Pleixats, J. Org. Chem., 60, 2396 (1995), see also references cited therein.
72. 2 and related complexes, see: a) M. C. Mazza and C. G. Pierpont, Inorg. Chem., 12, 2955 (1973); b) C. G. Pierpont and M. C. Mazza, Inorg. Chem., 13, 1891 (1974); c) F. Paul, J. Patt, and J. F. Hartwig, Organometallics, 14, 3030 (1995); d) M. Moreno-Mañas, F. Pajuelo, and R. Pleixats, J. Org. Chem., 60, 2396 (1995), see also references cited therein.
73. 2 and related complexes, see: a) M. C. Mazza and C. G. Pierpont, Inorg. Chem., 12, 2955 (1973); b) C. G. Pierpont and M. C. Mazza, Inorg. Chem., 13, 1891 (1974); c) F. Paul, J. Patt, and J. F. Hartwig, Organometallics, 14, 3030 (1995); d) M. Moreno-Mañas, F. Pajuelo, and R. Pleixats, J. Org. Chem., 60, 2396 (1995), see also references cited therein.
74. D. R. Coulson, Inorg. Synth., 13, 121 (1972).
75. M. L. Luetkens, Jr., A. P. Sattelberger, H. H. Murray, J. D. Basil, and J. P. Fackler, Jr., Inorg. Synth., 28, 305 (1990).
76. Both peaks of alcoholic protons in keto and enol form were not observed since the peaks were concealed behind other complicated peaks.
77. Y. Inoue, M. Toyofuku, M. Taguchi, S. Okada, and H. Hashimoto, Bull. Chem. Soc. Jpn., 59, 885 (1986).
78. 2H, shifts according to the concentration of the impurity (cinnamyl alcohol). The chemical shift of authentic sample 39 is δ=9.59 (br s).
79. The amine was deposited as its carbamate salt. See: M. Aresta and E. Quaranta, Tetrahedron, 48, 1515 (1992). See also references cited therein.