First isolation of a tris(ketyl) metal complex

Journal of the American Chemical Society

Volumn 118, Issue 33, 1996, Pages 7843-7844

  Hou, Zhaomin ^a   Fujita, Akira ^b   Yamazaki, Hiroshi ^b   Wakatsuki, Yasuo ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METAL COMPLEX;

ARTICLE; COMPLEX FORMATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0029794557     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9616185     Document Type: Article

References (25)

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6. Reviews: (a) Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 1.4. (c) Robertson, G. M. Ibid. Vol. 3, Chapter 2.6. (d) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (e) Kahn, B. E.; Riecke, R. T. Chem, Rev. 1988, 88, 733. (f) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (g) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399. (h) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. 1974, 7, 281. (i) House, H. O. In Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 3.
7. Reviews: (a) Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 1.4. (c) Robertson, G. M. Ibid. Vol. 3, Chapter 2.6. (d) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (e) Kahn, B. E.; Riecke, R. T. Chem, Rev. 1988, 88, 733. (f) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (g) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399. (h) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. 1974, 7, 281. (i) House, H. O. In Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 3.
8. Reviews: (a) Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 1.4. (c) Robertson, G. M. Ibid. Vol. 3, Chapter 2.6. (d) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (e) Kahn, B. E.; Riecke, R. T. Chem, Rev. 1988, 88, 733. (f) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (g) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399. (h) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. 1974, 7, 281. (i) House, H. O. In Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 3.
9. Reviews: (a) Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 1.4. (c) Robertson, G. M. Ibid. Vol. 3, Chapter 2.6. (d) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (e) Kahn, B. E.; Riecke, R. T. Chem, Rev. 1988, 88, 733. (f) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (g) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399. (h) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. 1974, 7, 281. (i) House, H. O. In Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 3.
10. Reviews: (a) Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 1.4. (c) Robertson, G. M. Ibid. Vol. 3, Chapter 2.6. (d) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (e) Kahn, B. E.; Riecke, R. T. Chem, Rev. 1988, 88, 733. (f) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (g) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399. (h) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. 1974, 7, 281. (i) House, H. O. In Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 3.
11. Reviews: (a) Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 1.4. (c) Robertson, G. M. Ibid. Vol. 3, Chapter 2.6. (d) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (e) Kahn, B. E.; Riecke, R. T. Chem, Rev. 1988, 88, 733. (f) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (g) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399. (h) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. 1974, 7, 281. (i) House, H. O. In Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 3.
12. Reviews: (a) Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 1.4. (c) Robertson, G. M. Ibid. Vol. 3, Chapter 2.6. (d) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (e) Kahn, B. E.; Riecke, R. T. Chem, Rev. 1988, 88, 733. (f) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (g) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399. (h) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. 1974, 7, 281. (i) House, H. O. In Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 3.
13. Reviews: (a) Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 1.4. (c) Robertson, G. M. Ibid. Vol. 3, Chapter 2.6. (d) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (e) Kahn, B. E.; Riecke, R. T. Chem, Rev. 1988, 88, 733. (f) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (g) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399. (h) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. 1974, 7, 281. (i) House, H. O. In Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 3.
14. Reviews: (a) Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164. (b) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, Chapter 1.4. (c) Robertson, G. M. Ibid. Vol. 3, Chapter 2.6. (d) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (e) Kahn, B. E.; Riecke, R. T. Chem, Rev. 1988, 88, 733. (f) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (g) Huffman, J. W. Acc. Chem. Res. 1983, 16, 399. (h) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405. 1974, 7, 281. (i) House, H. O. In Modern Synthetic Reactions, 2nd ed.; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 3.
15. For a recent overview on pinacol coupling, see: Wirth, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 61.
16. Hou, Z.; Miyano, T.; Yamazaki, H.; Wakatsuki, Y. J. Am. Chem. Soc. 1995, 117, 4421.
17. Hou, Z.; Fujita, A.; Yamazaki, H.; Wakatsuki, Y. J. Am. Chem. Soc. 1996, 118, 2503.
18. Hirota, N.; Weissman, S. I. J Am. Chem. Soc. 1964, 86, 2538.
19. 2I) in THF for 1 h. Addition of HMPA (1.06 mL, 6.1 mmol) to this blue suspension gave immediately a purple mixture to which a THF solution of fluorenone (1.08 g, 6 mmol) was syringed. The resulting dark green mixture was stirred at room temperature overnight and was filtered through a frit. Reduction of the solution volume under vacuum and addition of ether precipitated 1 (1.6 g, 65% yield) as black-green blocks. Using less than 3 equiv of HMPA also gave 1 as the only isolable product, but the yield was lower.
20. w = 0.0785).
21. Yoshimura, T.; Hou, Z.; Wakatsuki, Y. Organometallics 1995, 14, 5382.
22. Hou, Z.; Wakatsuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205.
23. Interactions among the three ketyl radicals in 1 were not observed by ESR spectroscopy at 22 to - 170 °C in either solid state or in THF.
24. Hou, Z.; Wakatsuki, Y. Unpublished results.
25. 8: δ 7.80-6.80 (m, 48 H, fluorenyl), 5.43 (s, 2H, CH), 2.57 (d, J = 8.0 Hz, 36 H, NMe).