Trapping of radicals in the coordination spheres of metals

Chemistry - A European Journal

Volumn 3, Issue 7, 1997, Pages 1005-1008

  Hou, Zhaomin ^a   Wakatsuki, Yasuo ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Alkali metals; Calcium; Ketyl radicals; Radicals; Samarium

Indexed keywords

EID: 0030877161     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030704     Document Type: Article

References (36)

1. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
2. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
3. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
4. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
5. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
6. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
7. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
8. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
9. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
10. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
11. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
12. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
13. For reviews on metal ketyl mediated organic synthesis, see: a) T. Wirth, Angew. Chem. 1996, 108, 65; Angen: Chem. Int. Ed. Engl. 1996, 35, 61; b) A. Fürstner, ibid. 1993, 105, 171 and 1993, 32, 164; c) J. W Huffman, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon: New York, 1991, Vol. 8, Chapt. 1.4. d) G. M. Robertson, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, Pergamon: New York, 1991, Vol. 3, Chapt. 2.6; e) J. E. McMurry, Chem. Rev. 1989, 89, 1513; f) B. E. Kahn, R. T. Riecke, ibid. 1988, 88, 733; g) S. K. Pradhan, Tetrahedron, 1986, 42, 6351; h) J. W. Huffman, Acc. Chem. Res. 1983, 16, 399; i) J. E. McMurry, ibid. 1983, 16, 405. 1974, 7, 281; j) H. O. House, in Modern Synthetic Reactions, 2nd ed.; W.A. Benjamin: Menlo Park, CA, 1972; Chapt. 3.
14. F. Bechman, T. Paul, Ann. 1891, 266, 1; W. Schlenk, T. Weichel, Ber. 1911, 44, 1182; W. Schlenk, A. Thal, ibid. 1913, 46, 2840.
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17. For examples see: K. Maruyama, T. Katagiri, J. Am. Chem. Soc. 1986, 108, 6263.
18. For examples of spectroscopic studies on metal ketyl species, see: a) P. H. Rieger, G. K. Fraenkel, J. Chem. Phy. 1962, 37, 2811; b) N. Hirota, S. I. Weissman, J. Am. Chem. Soc. 1964, 86, 2538; c) N. Hirota, ibid. 1967, 89, 32; d) S. W. Mao, K. Nakamura, N. Hirota, ibid. 1974, 96, 5341. e) K. J. Covert, P. T. Wolczanski, S. A. Hill, P. J. Krusic, Inorg. Chem. 1992, 31, 66.
19. For examples of spectroscopic studies on metal ketyl species, see: a) P. H. Rieger, G. K. Fraenkel, J. Chem. Phy. 1962, 37, 2811; b) N. Hirota, S. I. Weissman, J. Am. Chem. Soc. 1964, 86, 2538; c) N. Hirota, ibid. 1967, 89, 32; d) S. W. Mao, K. Nakamura, N. Hirota, ibid. 1974, 96, 5341. e) K. J. Covert, P. T. Wolczanski, S. A. Hill, P. J. Krusic, Inorg. Chem. 1992, 31, 66.
20. For examples of spectroscopic studies on metal ketyl species, see: a) P. H. Rieger, G. K. Fraenkel, J. Chem. Phy. 1962, 37, 2811; b) N. Hirota, S. I. Weissman, J. Am. Chem. Soc. 1964, 86, 2538; c) N. Hirota, ibid. 1967, 89, 32; d) S. W. Mao, K. Nakamura, N. Hirota, ibid. 1974, 96, 5341. e) K. J. Covert, P. T. Wolczanski, S. A. Hill, P. J. Krusic, Inorg. Chem. 1992, 31, 66.
21. For examples of spectroscopic studies on metal ketyl species, see: a) P. H. Rieger, G. K. Fraenkel, J. Chem. Phy. 1962, 37, 2811; b) N. Hirota, S. I. Weissman, J. Am. Chem. Soc. 1964, 86, 2538; c) N. Hirota, ibid. 1967, 89, 32; d) S. W. Mao, K. Nakamura, N. Hirota, ibid. 1974, 96, 5341. e) K. J. Covert, P. T. Wolczanski, S. A. Hill, P. J. Krusic, Inorg. Chem. 1992, 31, 66.
22. For examples of spectroscopic studies on metal ketyl species, see: a) P. H. Rieger, G. K. Fraenkel, J. Chem. Phy. 1962, 37, 2811; b) N. Hirota, S. I. Weissman, J. Am. Chem. Soc. 1964, 86, 2538; c) N. Hirota, ibid. 1967, 89, 32; d) S. W. Mao, K. Nakamura, N. Hirota, ibid. 1974, 96, 5341. e) K. J. Covert, P. T. Wolczanski, S. A. Hill, P. J. Krusic, Inorg. Chem. 1992, 31, 66.
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24. Z. Hou, A. Fujita, H. Yamazaki, Y. Wakatsuki, unpublished results. HMPA should be handled with care, since it is suspected of a carcinogen.
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26. Z. Hou, A. Fujita, H. Yamazaki, Y. Wakatsuki, 17th International Conference on Organometallic Chemistry, 1995, PA1-4; Abstract, p. 107.
27. Z. Hou, X. Jia, Y. Wakatsuki, unpublished results.
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