First isolation of a metal ketyl in aggregated forms. X-ray structures of dimeric and tetrameric sodium fluorenone ketyl complexes: [Na(μ2-η1-ketyl)(HMPA)2]2 and [Na(μ3-η1-ketyl)(HMPA)]4

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2503-2504

  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

ACETAL; ALKALI METAL; METAL COMPLEX;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; X RAY ANALYSIS;

EID: 0029879365     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953931x     Document Type: Article

References (30)

1. (a) Bechman, F.; Paul. T. Justus Liebigs Ann. Chem. 1891, 266, 1.
2. (b) Schlenk, W.; Weichel, T. Ber. Dtsch. Chem. Ges. 1911, 44, 1182.
3. (c) Schlenk, W.; Thal, A. Ber. Dtsch. Chem. Ges. 1913, 46, 2480.
4. Reviews on metal ketyl-involved organic synthesis: (a) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8. Chapter 1.4. (b) Robertson, G. M. In Comprehensive Organic Synthesis: Trost. B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (d) Kahn, B. E.; Riecke, R. T. Chem. Rev. 1988, 88, 733. (e) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (f) Huffman, J. W. Ace. Chem. Res. 1983, 16, 399. (g) McMurry, J. E. Ace. Chem. Res. 1983, 16, 405; 1974, 7, 281. (h) House, H. O. Modem Synthetic Reactions, 2nd ed.; W. A. Benjamin; Menlo Park, CA, 1972; Chapter 3.
5. Reviews on metal ketyl-involved organic synthesis: (a) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8. Chapter 1.4. (b) Robertson, G. M. In Comprehensive Organic Synthesis: Trost. B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (d) Kahn, B. E.; Riecke, R. T. Chem. Rev. 1988, 88, 733. (e) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (f) Huffman, J. W. Ace. Chem. Res. 1983, 16, 399. (g) McMurry, J. E. Ace. Chem. Res. 1983, 16, 405; 1974, 7, 281. (h) House, H. O. Modem Synthetic Reactions, 2nd ed.; W. A. Benjamin; Menlo Park, CA, 1972; Chapter 3.
6. Reviews on metal ketyl-involved organic synthesis: (a) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8. Chapter 1.4. (b) Robertson, G. M. In Comprehensive Organic Synthesis: Trost. B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (d) Kahn, B. E.; Riecke, R. T. Chem. Rev. 1988, 88, 733. (e) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (f) Huffman, J. W. Ace. Chem. Res. 1983, 16, 399. (g) McMurry, J. E. Ace. Chem. Res. 1983, 16, 405; 1974, 7, 281. (h) House, H. O. Modem Synthetic Reactions, 2nd ed.; W. A. Benjamin; Menlo Park, CA, 1972; Chapter 3.
7. Reviews on metal ketyl-involved organic synthesis: (a) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8. Chapter 1.4. (b) Robertson, G. M. In Comprehensive Organic Synthesis: Trost. B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (d) Kahn, B. E.; Riecke, R. T. Chem. Rev. 1988, 88, 733. (e) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (f) Huffman, J. W. Ace. Chem. Res. 1983, 16, 399. (g) McMurry, J. E. Ace. Chem. Res. 1983, 16, 405; 1974, 7, 281. (h) House, H. O. Modem Synthetic Reactions, 2nd ed.; W. A. Benjamin; Menlo Park, CA, 1972; Chapter 3.
8. Reviews on metal ketyl-involved organic synthesis: (a) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8. Chapter 1.4. (b) Robertson, G. M. In Comprehensive Organic Synthesis: Trost. B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (d) Kahn, B. E.; Riecke, R. T. Chem. Rev. 1988, 88, 733. (e) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (f) Huffman, J. W. Ace. Chem. Res. 1983, 16, 399. (g) McMurry, J. E. Ace. Chem. Res. 1983, 16, 405; 1974, 7, 281. (h) House, H. O. Modem Synthetic Reactions, 2nd ed.; W. A. Benjamin; Menlo Park, CA, 1972; Chapter 3.
9. Reviews on metal ketyl-involved organic synthesis: (a) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8. Chapter 1.4. (b) Robertson, G. M. In Comprehensive Organic Synthesis: Trost. B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (d) Kahn, B. E.; Riecke, R. T. Chem. Rev. 1988, 88, 733. (e) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (f) Huffman, J. W. Ace. Chem. Res. 1983, 16, 399. (g) McMurry, J. E. Ace. Chem. Res. 1983, 16, 405; 1974, 7, 281. (h) House, H. O. Modem Synthetic Reactions, 2nd ed.; W. A. Benjamin; Menlo Park, CA, 1972; Chapter 3.
10. Reviews on metal ketyl-involved organic synthesis: (a) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8. Chapter 1.4. (b) Robertson, G. M. In Comprehensive Organic Synthesis: Trost. B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (d) Kahn, B. E.; Riecke, R. T. Chem. Rev. 1988, 88, 733. (e) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (f) Huffman, J. W. Ace. Chem. Res. 1983, 16, 399. (g) McMurry, J. E. Ace. Chem. Res. 1983, 16, 405; 1974, 7, 281. (h) House, H. O. Modem Synthetic Reactions, 2nd ed.; W. A. Benjamin; Menlo Park, CA, 1972; Chapter 3.
11. Reviews on metal ketyl-involved organic synthesis: (a) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8. Chapter 1.4. (b) Robertson, G. M. In Comprehensive Organic Synthesis: Trost. B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (d) Kahn, B. E.; Riecke, R. T. Chem. Rev. 1988, 88, 733. (e) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (f) Huffman, J. W. Ace. Chem. Res. 1983, 16, 399. (g) McMurry, J. E. Ace. Chem. Res. 1983, 16, 405; 1974, 7, 281. (h) House, H. O. Modem Synthetic Reactions, 2nd ed.; W. A. Benjamin; Menlo Park, CA, 1972; Chapter 3.
12. Reviews on metal ketyl-involved organic synthesis: (a) Huffman, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8. Chapter 1.4. (b) Robertson, G. M. In Comprehensive Organic Synthesis: Trost. B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 3, Chapter 2.6. (c) McMurry, J. E. Chem. Rev. 1989, 89, 1513. (d) Kahn, B. E.; Riecke, R. T. Chem. Rev. 1988, 88, 733. (e) Pradhan, S. K. Tetrahedron 1986, 42, 6351. (f) Huffman, J. W. Ace. Chem. Res. 1983, 16, 399. (g) McMurry, J. E. Ace. Chem. Res. 1983, 16, 405; 1974, 7, 281. (h) House, H. O. Modem Synthetic Reactions, 2nd ed.; W. A. Benjamin; Menlo Park, CA, 1972; Chapter 3.
13. Sodium benzophenone ketyl is used in almost every chemistry laboratory for dehydration of etheral solvents.
14. For examples, see: (a) Hirota, N.; Weissman, S. I. J. Am. Chem. Soc. 1964, 86, 2538. (b) Hirota, N. J. Am. Chem. Soc. 1967, 89, 32.
15. For examples, see: (a) Hirota, N.; Weissman, S. I. J. Am. Chem. Soc. 1964, 86, 2538. (b) Hirota, N. J. Am. Chem. Soc. 1967, 89, 32.
16. Coutts, R. S. P.; Wailes, P. C.; Martin, R. L. J. Organomet. Chem. 1973, 50, 145.
17. (a) Hillgärtner, H; Newmann, W. P.; Schröder, B. Liebigs Ann. Chem. 1975, 586,
18. (b) Ziebarth, M; Newmann, W. P. Liebigs Ann. Chem. 1978, 1765.
19. Huffman, J. C.; Moloy, K. G.; Marsella, J. A.; Caulton. K. G. J. Am. Chem. Soc. 1980, 102, 3009.
20. Anderson, L. B.; Cotton, F. A.; DeMarco, D.; Falvello, L. R.; Tetrick, S. M.; Walton, R. A. J. Am. Chem. Soc. 1984, 106, 4743.
21. Hou, Z.; Miyano, T.; Yamazaki, H.; Wakatsuki, Y. J. Am. Chem. Soc. 1995, 117, 4421.
22. Crystals suitable for X-ray analysis were not obtained without using HMPA.
23. For UV-vis and ESR spectra and microelemental analysis data for 1 and 2. see supporting information.
24. w = 0.1179).
25. Brooker, S.; Edelmann, F. T.; Kottke, T.; Roesky, H. W.; Scheldrick, G. M.; Stalke, D.; Whitmire, K. H. J. Chem. Soc., Chem. Commun. 1991, 144.
26. Yoshimura, T.; Hou, Z.; Wakatsuki, Y. Organometallics 1995, 14, 5382.
27. Hou, Z.; Fujita, A.; Yamazaki. H.; Wakatsuki, Y. Unpublished results.
28. Barr, D.; Doyle, M. J.; Drake, S. R.; Raithby, P. R.; Snaith, R.; Wright. D. S. Polyhedron 1989, 8, 215.
29. Williard, P. G.; Carpenter, G. B. J. Am. Chem. Soc. 1986, 108, 462.
30. Hou, Z.; Wakatsuki, Y. J. Synth, Org. Chem., Jpn. 1995, 53, 906.