Reduction of 2,5-di-tert-butylcyclopentadienone and pyridine with thulium diiodide (see abstract)

Russian Chemical Bulletin

Volumn 52, Issue 1, 2003, Pages 154-159

  Fedushkin, I L ^a   Nevodchikov, V I ^a   Bochkarev, M N ^a   Dechert, S ^b   Schumann, H ^b  

^a G A RAZUVAEV INSTITUTE OF ORGANOMETALLIC CHEMISTRY   (Russian Federation)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Cyclopentadienone; Pyridine; Reduction; Thulium

Indexed keywords

2,5 DI TERT BUTYLCYCLOPENTADIENONE; ANION; BIS[TETRAKIS(PYRIDINE)THULIUM DIIODIDE] 1,1' DIHYDRO 4,4' BIPYRIDYL; CARBON; IODINE DERIVATIVE; KETONE DERIVATIVE; PYRIDINE; PYRIDINE DERIVATIVE; TETRAHYDROFURAN; THULIUM DIIODIDE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; REDUCTION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 1642576237     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1022408717918     Document Type: Article

References (40)

1. G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. Harris, Chem. Rev., 1996, 96, 307; B. Hamman-Gaudient, J.-L. Namy, and H. B. Kagan, J. Organomet. Chem., 1998, 567, 39; H.-G. Schmalz, S. Siegel, and J. W. Bats, Angew. Chem., Int. Ed., 1995, 34, 2383; H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
2. G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. Harris, Chem. Rev., 1996, 96, 307; B. Hamman-Gaudient, J.-L. Namy, and H. B. Kagan, J. Organomet. Chem., 1998, 567, 39; H.-G. Schmalz, S. Siegel, and J. W. Bats, Angew. Chem., Int. Ed., 1995, 34, 2383; H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
3. G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. Harris, Chem. Rev., 1996, 96, 307; B. Hamman-Gaudient, J.-L. Namy, and H. B. Kagan, J. Organomet. Chem., 1998, 567, 39; H.-G. Schmalz, S. Siegel, and J. W. Bats, Angew. Chem., Int. Ed., 1995, 34, 2383; H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
4. G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. Harris, Chem. Rev., 1996, 96, 307; B. Hamman-Gaudient, J.-L. Namy, and H. B. Kagan, J. Organomet. Chem., 1998, 567, 39; H.-G. Schmalz, S. Siegel, and J. W. Bats, Angew. Chem., Int. Ed., 1995, 34, 2383; H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
5. G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. Harris, Chem. Rev., 1996, 96, 307; B. Hamman-Gaudient, J.-L. Namy, and H. B. Kagan, J. Organomet. Chem., 1998, 567, 39; H.-G. Schmalz, S. Siegel, and J. W. Bats, Angew. Chem., Int. Ed., 1995, 34, 2383; H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
6. G. A. Molander, Chem. Rev., 1992, 92, 29; G. A. Molander and C. Harris, Chem. Rev., 1996, 96, 307; B. Hamman-Gaudient, J.-L. Namy, and H. B. Kagan, J. Organomet. Chem., 1998, 567, 39; H.-G. Schmalz, S. Siegel, and J. W. Bats, Angew. Chem., Int. Ed., 1995, 34, 2383; H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573; A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
7. M. N. Bochkarev, I. L. Fedushkin, A. A. Fagin, T. V. Petrovskaya, J. W. Ziller, R. N. R. Broohall-Dillard, and W. J. Evans, Angew. Chem., Int. Ed., 1997, 35, 133; M. N. Bochkarev and A. A. Fagin, Chem. Eur. J., 1999, 5, 2990; M. N. Bochkarev, I. L. Fedushkin, S. Dechert, A. A. Fagin, and H. Schumann, Angew. Chem., Int. Ed., 2001, 40, 3176.
8. M. N. Bochkarev, I. L. Fedushkin, A. A. Fagin, T. V. Petrovskaya, J. W. Ziller, R. N. R. Broohall-Dillard, and W. J. Evans, Angew. Chem., Int. Ed., 1997, 35, 133; M. N. Bochkarev and A. A. Fagin, Chem. Eur. J., 1999, 5, 2990; M. N. Bochkarev, I. L. Fedushkin, S. Dechert, A. A. Fagin, and H. Schumann, Angew. Chem., Int. Ed., 2001, 40, 3176.
9. M. N. Bochkarev, I. L. Fedushkin, A. A. Fagin, T. V. Petrovskaya, J. W. Ziller, R. N. R. Broohall-Dillard, and W. J. Evans, Angew. Chem., Int. Ed., 1997, 35, 133; M. N. Bochkarev and A. A. Fagin, Chem. Eur. J., 1999, 5, 2990; M. N. Bochkarev, I. L. Fedushkin, S. Dechert, A. A. Fagin, and H. Schumann, Angew. Chem., Int. Ed., 2001, 40, 3176.
10. I. L. Fedushkin, M. N. Bochkarev, S. Dechert, and H. Schumann, Chem. Eur. J., 2001, 7, 3558.
11. W. J. Evans and N. T. Allen, J. Am. Chem. Soc., 2000, 122, 2118.
12. Z. Hou, A. Fujita, Y. Zhang, T. Miyano, H. Yamazaki, and Y. Wakatsuki, J. Am. Chem. Soc., 1998, 120, 754.
13. (a) A. A. Koridze, T. T. Efremidze, Yu. T. Struchkov, and A. I. Yanovsky, Metalloorg. Khim., 1988, 1, 826 [Organomet. Chem. USSR, 1988, 1, 826 (Engl. Transl.)];
14. (a) A. A. Koridze, T. T. Efremidze, Yu. T. Struchkov, and A. I. Yanovsky, Metalloorg. Khim., 1988, 1, 826 [Organomet. Chem. USSR, 1988, 1, 826 (Engl. Transl.)];
15. (b) H.-J. Knölker, E. Baum, H. Goesmann, and R. Klauss, Angew. Chem., Int. Ed., 1999, 38, 2064.
16. M. N. Bochkarev, L. N. Zakharov, and G. S. Kalinina, Organoderivatives of Rare Earth Elements, Kluwer Academic Publishers, Dordrecht, 1995, 530; H. Schumann, J. A. Meese-Marktscheffel, and L. Esser, Chem. Rev., 1995, 95, 865.
17. M. N. Bochkarev, L. N. Zakharov, and G. S. Kalinina, Organoderivatives of Rare Earth Elements, Kluwer Academic Publishers, Dordrecht, 1995, 530; H. Schumann, J. A. Meese-Marktscheffel, and L. Esser, Chem. Rev., 1995, 95, 865.
18. Z. Xie, Ka-yue Chiu, B. Wu, and T. C. W. Mak, Inorg. Chem., 1996, 35, 5957; S. Anfang, M. Karl, N. Faza, W. Massa, J. Magull, and K. Dehnicke, Z. Anorg. Allg. Chem., 1997, 623, 1425; W. J. Evans, T. J. Boyle, and J. W. Ziller, J. Am. Chem. Soc., 1993, 115, 5084; S.-H. Lin, Z.-C. Dong, J.-S. Huang, Q.-E. Zhang, and X.-L. Lu, Acta Crystallogr. Sect. C - Cryst. Struct. Commun., 1991, C47, 426; C. Wenqi, X. Y. Zhongsheng, and F. Yuguo, Inorg. Chim. Acta, 1987, 130, 125; Z. Jin, G. Nie, N. Hu, and W. Chen, Chin. J. Appl. Chem. (Yingyong Huaxue), 1989, 6, 68; W. J. Evans, J. L. Shreeve, J. W. Ziller, and R. J. Doedens, Inorg. Chem., 1995, 34, 576; W. J. Evans, J. M. Olofson, and J. W. Ziller, J. Am. Chem. Soc., 1990, 112, 2308.
19. Z. Xie, Ka-yue Chiu, B. Wu, and T. C. W. Mak, Inorg. Chem., 1996, 35, 5957; S. Anfang, M. Karl, N. Faza, W. Massa, J. Magull, and K. Dehnicke, Z. Anorg. Allg. Chem., 1997, 623, 1425; W. J. Evans, T. J. Boyle, and J. W. Ziller, J. Am. Chem. Soc., 1993, 115, 5084; S.-H. Lin, Z.-C. Dong, J.-S. Huang, Q.-E. Zhang, and X.-L. Lu, Acta Crystallogr. Sect. C - Cryst. Struct. Commun., 1991, C47, 426; C. Wenqi, X. Y. Zhongsheng, and F. Yuguo, Inorg. Chim. Acta, 1987, 130, 125; Z. Jin, G. Nie, N. Hu, and W. Chen, Chin. J. Appl. Chem. (Yingyong Huaxue), 1989, 6, 68; W. J. Evans, J. L. Shreeve, J. W. Ziller, and R. J. Doedens, Inorg. Chem., 1995, 34, 576; W. J. Evans, J. M. Olofson, and J. W. Ziller, J. Am. Chem. Soc., 1990, 112, 2308.
20. Z. Xie, Ka-yue Chiu, B. Wu, and T. C. W. Mak, Inorg. Chem., 1996, 35, 5957; S. Anfang, M. Karl, N. Faza, W. Massa, J. Magull, and K. Dehnicke, Z. Anorg. Allg. Chem., 1997, 623, 1425; W. J. Evans, T. J. Boyle, and J. W. Ziller, J. Am. Chem. Soc., 1993, 115, 5084; S.-H. Lin, Z.-C. Dong, J.-S. Huang, Q.-E. Zhang, and X.-L. Lu, Acta Crystallogr. Sect. C - Cryst. Struct. Commun., 1991, C47, 426; C. Wenqi, X. Y. Zhongsheng, and F. Yuguo, Inorg. Chim. Acta, 1987, 130, 125; Z. Jin, G. Nie, N. Hu, and W. Chen, Chin. J. Appl. Chem. (Yingyong Huaxue), 1989, 6, 68; W. J. Evans, J. L. Shreeve, J. W. Ziller, and R. J. Doedens, Inorg. Chem., 1995, 34, 576; W. J. Evans, J. M. Olofson, and J. W. Ziller, J. Am. Chem. Soc., 1990, 112, 2308.
21. Z. Xie, Ka-yue Chiu, B. Wu, and T. C. W. Mak, Inorg. Chem., 1996, 35, 5957; S. Anfang, M. Karl, N. Faza, W. Massa, J. Magull, and K. Dehnicke, Z. Anorg. Allg. Chem., 1997, 623, 1425; W. J. Evans, T. J. Boyle, and J. W. Ziller, J. Am. Chem. Soc., 1993, 115, 5084; S.-H. Lin, Z.-C. Dong, J.-S. Huang, Q.-E. Zhang, and X.-L. Lu, Acta Crystallogr. Sect. C - Cryst. Struct. Commun., 1991, C47, 426; C. Wenqi, X. Y. Zhongsheng, and F. Yuguo, Inorg. Chim. Acta, 1987, 130, 125; Z. Jin, G. Nie, N. Hu, and W. Chen, Chin. J. Appl. Chem. (Yingyong Huaxue), 1989, 6, 68; W. J. Evans, J. L. Shreeve, J. W. Ziller, and R. J. Doedens, Inorg. Chem., 1995, 34, 576; W. J. Evans, J. M. Olofson, and J. W. Ziller, J. Am. Chem. Soc., 1990, 112, 2308.
22. Z. Xie, Ka-yue Chiu, B. Wu, and T. C. W. Mak, Inorg. Chem., 1996, 35, 5957; S. Anfang, M. Karl, N. Faza, W. Massa, J. Magull, and K. Dehnicke, Z. Anorg. Allg. Chem., 1997, 623, 1425; W. J. Evans, T. J. Boyle, and J. W. Ziller, J. Am. Chem. Soc., 1993, 115, 5084; S.-H. Lin, Z.-C. Dong, J.-S. Huang, Q.-E. Zhang, and X.-L. Lu, Acta Crystallogr. Sect. C - Cryst. Struct. Commun., 1991, C47, 426; C. Wenqi, X. Y. Zhongsheng, and F. Yuguo, Inorg. Chim. Acta, 1987, 130, 125; Z. Jin, G. Nie, N. Hu, and W. Chen, Chin. J. Appl. Chem. (Yingyong Huaxue), 1989, 6, 68; W. J. Evans, J. L. Shreeve, J. W. Ziller, and R. J. Doedens, Inorg. Chem., 1995, 34, 576; W. J. Evans, J. M. Olofson, and J. W. Ziller, J. Am. Chem. Soc., 1990, 112, 2308.
23. Z. Xie, Ka-yue Chiu, B. Wu, and T. C. W. Mak, Inorg. Chem., 1996, 35, 5957; S. Anfang, M. Karl, N. Faza, W. Massa, J. Magull, and K. Dehnicke, Z. Anorg. Allg. Chem., 1997, 623, 1425; W. J. Evans, T. J. Boyle, and J. W. Ziller, J. Am. Chem. Soc., 1993, 115, 5084; S.-H. Lin, Z.-C. Dong, J.-S. Huang, Q.-E. Zhang, and X.-L. Lu, Acta Crystallogr. Sect. C - Cryst. Struct. Commun., 1991, C47, 426; C. Wenqi, X. Y. Zhongsheng, and F. Yuguo, Inorg. Chim. Acta, 1987, 130, 125; Z. Jin, G. Nie, N. Hu, and W. Chen, Chin. J. Appl. Chem. (Yingyong Huaxue), 1989, 6, 68; W. J. Evans, J. L. Shreeve, J. W. Ziller, and R. J. Doedens, Inorg. Chem., 1995, 34, 576; W. J. Evans, J. M. Olofson, and J. W. Ziller, J. Am. Chem. Soc., 1990, 112, 2308.
24. Z. Xie, Ka-yue Chiu, B. Wu, and T. C. W. Mak, Inorg. Chem., 1996, 35, 5957; S. Anfang, M. Karl, N. Faza, W. Massa, J. Magull, and K. Dehnicke, Z. Anorg. Allg. Chem., 1997, 623, 1425; W. J. Evans, T. J. Boyle, and J. W. Ziller, J. Am. Chem. Soc., 1993, 115, 5084; S.-H. Lin, Z.-C. Dong, J.-S. Huang, Q.-E. Zhang, and X.-L. Lu, Acta Crystallogr. Sect. C - Cryst. Struct. Commun., 1991, C47, 426; C. Wenqi, X. Y. Zhongsheng, and F. Yuguo, Inorg. Chim. Acta, 1987, 130, 125; Z. Jin, G. Nie, N. Hu, and W. Chen, Chin. J. Appl. Chem. (Yingyong Huaxue), 1989, 6, 68; W. J. Evans, J. L. Shreeve, J. W. Ziller, and R. J. Doedens, Inorg. Chem., 1995, 34, 576; W. J. Evans, J. M. Olofson, and J. W. Ziller, J. Am. Chem. Soc., 1990, 112, 2308.
25. Z. Xie, Ka-yue Chiu, B. Wu, and T. C. W. Mak, Inorg. Chem., 1996, 35, 5957; S. Anfang, M. Karl, N. Faza, W. Massa, J. Magull, and K. Dehnicke, Z. Anorg. Allg. Chem., 1997, 623, 1425; W. J. Evans, T. J. Boyle, and J. W. Ziller, J. Am. Chem. Soc., 1993, 115, 5084; S.-H. Lin, Z.-C. Dong, J.-S. Huang, Q.-E. Zhang, and X.-L. Lu, Acta Crystallogr. Sect. C - Cryst. Struct. Commun., 1991, C47, 426; C. Wenqi, X. Y. Zhongsheng, and F. Yuguo, Inorg. Chim. Acta, 1987, 130, 125; Z. Jin, G. Nie, N. Hu, and W. Chen, Chin. J. Appl. Chem. (Yingyong Huaxue), 1989, 6, 68; W. J. Evans, J. L. Shreeve, J. W. Ziller, and R. J. Doedens, Inorg. Chem., 1995, 34, 576; W. J. Evans, J. M. Olofson, and J. W. Ziller, J. Am. Chem. Soc., 1990, 112, 2308.
26. M. N. Bochkarev, A. A. Fagin, I. L. Fedushkin, T. V. Petrovskaya, W. J. Evans, M. A. Greci, and J. W. Ziller, Izv. Akad. Nauk, Ser. Khim., 1999, 1804 [Russ. Chem. Bull., 1999, 48, 1782 (Engl. Transl.)].
27. M. N. Bochkarev, A. A. Fagin, I. L. Fedushkin, T. V. Petrovskaya, W. J. Evans, M. A. Greci, and J. W. Ziller, Izv. Akad. Nauk, Ser. Khim., 1999, 1804 [Russ. Chem. Bull., 1999, 48, 1782 (Engl. Transl.)].
28. I. L. Fedushkin, F. Girgsdies, H. Schumann, and M. N. Bochkarev, Eur. J. Inorg. Chem., 2001, 9, 2405.
29. I. L. Fedushkin, M. Weydert, A. A. Fagin, S. E. Nefedov, I. L. Eremenko, M. N. Bochkarev, and H. Schumann, Z. Naturforsch., 1999, 54b, 466.
30. U. Siemeling, Chem. Rev., 2000, 100, 1495.
31. W. J. Evans, R. N. R. Broomhall-Dillard, and J. W. Ziller, Polyhedron, 1998, 17, 3361.
32. W. J. Evans and M. A. Horzbor, J. Organomet. Chem., 1987, 326, 299.
33. M. N. Bochkarev, I. L. Fedushkin, A. A. Fagin, H. Schumann, and J. Demtschuk, J. Chem. Soc., Chem. Commun., 1997, 1783.
34. W. J. Evans, S. L. Gonzales, and J. W. Ziller, J. Am. Chem. Soc., 1994, 116, 2600.
35. P. B. Hitchcock, M. F. Lappert, and A. V. Protchenko, J. Am. Chem. Soc., 2000, 123, 189.
36. A. V. Protchenko and M. N. Bochkarev, Pribory Tekh. Eksp. [Appar. Techn. Exp.], 1990, 1, 194 (in Russian).
37. G. M. Sheldrick, SADABS Program for Empirical Absorption Correction of Area Detector Data; Universität Göttingen, 1996.
38. G. M. Sheldrick, SHELXS-97 Program for the Solution of Crystal Structures, Universität Göttingen, 1990.
39. G. M. Sheldrick, SHELXL-97 Program for Crystal Structure Refinement, Universität Göttingen, 1997.
40. A. L. Spek, Acta Crystallogr., 1990, A46, C-34.