Photocatalytic hydrosilylation of conjugated dienes with triethylsilane in the presence of Cr(CO)6

Organometallics

Volumn 15, Issue 2, 1996, Pages 604-614

  Abdelqader, Wafa ^a   Chmielewski, Dietmar ^b   Grevels, Friedrich Wilhelm ^b   Özkar, Saim ^a   Peynircioglu, Nihad Bekir ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^b MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001403417     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950369a     Document Type: Article

References (48)

1. Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1989; Vol. 2, Chapter 25, pp 1479-1526.
2. Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1993; Vol. 8, Chapter 3.12, pp 763-792.
3. Harrod, J. F. In Encyclopedia of Inorganic Chemistry; King, R. B., Ed.; Wiley: Chichester, U.K., 1994; Vol. 3, pp 1486-1496.
4. Harrod, J. F.; Chalk, A. J. In Organic Syntheses via Metal Carbonyls; Wender, I., Pino, P., Eds.; Wiley: New York, 1977; Vol. 2, pp 673-704.
5. Schroeder, M. A.; Wrighton, M. S. J. Organomet. Chem. 1977, 128, 345-358.
6. Seitz, F.; Wrighton, M. A. Angew. Chem. 1988, 100, 281-283; Angew. Chem., Int. Ed. Engl. 1988, 27, 289.
7. Seitz, F.; Wrighton, M. A. Angew. Chem. 1988, 100, 281-283; Angew. Chem., Int. Ed. Engl. 1988, 27, 289.
8. Duckett, S. B.; Perutz, R. N. Organometallics 1992, 11, 90-98.
9. Abdelqader, W.; Özkar, S.; Peynircioglu, N. B. Z. Naturforsch. 1993, 48B, 539-540.
10. Wrighton, M. S.; Schroeder, M. A. J. Am. Chem. Soc. 1974, 96, 6235-6237.
11. Alberts, V.; Cuthbertson, M. J.; Hawker, D. W.; Wells, P. R. Org. Magn. Reson. 1984, 22, 556-560.
12. Fischler, I.; Grevels, F.-W. J. Organomet. Chem. 1980, 204, 181-190.
13. Günther, H. NMR Spectroscopy; Wiley: New York, 1980; p 373.
14. Koerner von Gustorf, E. A.; Jaenicke, O.; Wolfbeis, O.; Eady, C. R. Angew. Chem. 1975, 87, 300-306. Kotzian, M.; Kreiter, C. G.; Özkar, S. J. Organomet. Chem. 1982, 229, 29-42.
15. Koerner von Gustorf, E. A.; Jaenicke, O.; Wolfbeis, O.; Eady, C. R. Angew. Chem. 1975, 87, 300-306. Kotzian, M.; Kreiter, C. G.; Özkar, S. J. Organomet. Chem. 1982, 229, 29-42.
16. Özkar, S.; Peynircioglu, N. B. Inorg. Chim. Acta 1986, 119, 127-129.
17. Grevels, F.-W.; Özkar, S. Unpublished results.
18. Platbrood, G.; Wilputte-Steinert, L. Bull. Soc. Chim. Belg. 1973 82, 733-735. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 393-405. Darensbourg, D. J.; Nelson, H. H., III; Murphy, M. A. J. Am. Chem. Soc. 1977, 99, 896-903. Mirbach, M. J.; Steinmetz, D.; Saus, A. J. Organomet. Chem. 1979, 168, C13-C15. Mirbach, M. J.; Phu, T. N.; Saus, A. J. Organomet. Chem. 1982, 236, 309-320.
19. Platbrood, G.; Wilputte-Steinert, L. Bull. Soc. Chim. Belg. 1973 82, 733-735. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 393-405. Darensbourg, D. J.; Nelson, H. H., III; Murphy, M. A. J. Am. Chem. Soc. 1977, 99, 896-903. Mirbach, M. J.; Steinmetz, D.; Saus, A. J. Organomet. Chem. 1979, 168, C13-C15. Mirbach, M. J.; Phu, T. N.; Saus, A. J. Organomet. Chem. 1982, 236, 309-320.
20. Platbrood, G.; Wilputte-Steinert, L. Bull. Soc. Chim. Belg. 1973 82, 733-735. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 393-405. Darensbourg, D. J.; Nelson, H. H., III; Murphy, M. A. J. Am. Chem. Soc. 1977, 99, 896-903. Mirbach, M. J.; Steinmetz, D.; Saus, A. J. Organomet. Chem. 1979, 168, C13-C15. Mirbach, M. J.; Phu, T. N.; Saus, A. J. Organomet. Chem. 1982, 236, 309-320.
21. Platbrood, G.; Wilputte-Steinert, L. Bull. Soc. Chim. Belg. 1973 82, 733-735. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 393-405. Darensbourg, D. J.; Nelson, H. H., III; Murphy, M. A. J. Am. Chem. Soc. 1977, 99, 896-903. Mirbach, M. J.; Steinmetz, D.; Saus, A. J. Organomet. Chem. 1979, 168, C13-C15. Mirbach, M. J.; Phu, T. N.; Saus, A. J. Organomet. Chem. 1982, 236, 309-320.
22. Platbrood, G.; Wilputte-Steinert, L. Bull. Soc. Chim. Belg. 1973 82, 733-735. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 393-405. Darensbourg, D. J.; Nelson, H. H., III; Murphy, M. A. J. Am. Chem. Soc. 1977, 99, 896-903. Mirbach, M. J.; Steinmetz, D.; Saus, A. J. Organomet. Chem. 1979, 168, C13-C15. Mirbach, M. J.; Phu, T. N.; Saus, A. J. Organomet. Chem. 1982, 236, 309-320.
23. Nasielski, J.; Kirsch, P.; Wilputte-Steinert, L. J. Organomet. Chem. 1971, 27, C13-14. Platbrood, G.; Wilputte-Steinert, L. Tetrahedron Lett. 1974, 2507-2508. Wrighton, M.; Schroeder, M. A. J. Am. Chem. Soc. 1973, 95, 5764-5765. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 407-412. Platbrood, G.; Wilputte-Steinert, L. J. Mol. Catal. 1975/76, 1, 265-273. Fischler, I.; Budzwait, M.; Koerner von Gustorf, E. A. J. Organomet. Chem. 1976, 105, 325-330.
24. Nasielski, J.; Kirsch, P.; Wilputte-Steinert, L. J. Organomet. Chem. 1971, 27, C13-14. Platbrood, G.; Wilputte-Steinert, L. Tetrahedron Lett. 1974, 2507-2508. Wrighton, M.; Schroeder, M. A. J. Am. Chem. Soc. 1973, 95, 5764-5765. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 407-412. Platbrood, G.; Wilputte-Steinert, L. J. Mol. Catal. 1975/76, 1, 265-273. Fischler, I.; Budzwait, M.; Koerner von Gustorf, E. A. J. Organomet. Chem. 1976, 105, 325-330.
25. Nasielski, J.; Kirsch, P.; Wilputte-Steinert, L. J. Organomet. Chem. 1971, 27, C13-14. Platbrood, G.; Wilputte-Steinert, L. Tetrahedron Lett. 1974, 2507-2508. Wrighton, M.; Schroeder, M. A. J. Am. Chem. Soc. 1973, 95, 5764-5765. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 407-412. Platbrood, G.; Wilputte-Steinert, L. J. Mol. Catal. 1975/76, 1, 265-273. Fischler, I.; Budzwait, M.; Koerner von Gustorf, E. A. J. Organomet. Chem. 1976, 105, 325-330.
26. Nasielski, J.; Kirsch, P.; Wilputte-Steinert, L. J. Organomet. Chem. 1971, 27, C13-14. Platbrood, G.; Wilputte-Steinert, L. Tetrahedron Lett. 1974, 2507-2508. Wrighton, M.; Schroeder, M. A. J. Am. Chem. Soc. 1973, 95, 5764-5765. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 407-412. Platbrood, G.; Wilputte-Steinert, L. J. Mol. Catal. 1975/76, 1, 265-273. Fischler, I.; Budzwait, M.; Koerner von Gustorf, E. A. J. Organomet. Chem. 1976, 105, 325-330.
27. Nasielski, J.; Kirsch, P.; Wilputte-Steinert, L. J. Organomet. Chem. 1971, 27, C13-14. Platbrood, G.; Wilputte-Steinert, L. Tetrahedron Lett. 1974, 2507-2508. Wrighton, M.; Schroeder, M. A. J. Am. Chem. Soc. 1973, 95, 5764-5765. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 407-412. Platbrood, G.; Wilputte-Steinert, L. J. Mol. Catal. 1975/76, 1, 265-273. Fischler, I.; Budzwait, M.; Koerner von Gustorf, E. A. J. Organomet. Chem. 1976, 105, 325-330.
28. Nasielski, J.; Kirsch, P.; Wilputte-Steinert, L. J. Organomet. Chem. 1971, 27, C13-14. Platbrood, G.; Wilputte-Steinert, L. Tetrahedron Lett. 1974, 2507-2508. Wrighton, M.; Schroeder, M. A. J. Am. Chem. Soc. 1973, 95, 5764-5765. Platbrood, G.; Wilputte-Steinert, L. J. Organomet. Chem. 1974, 70, 407-412. Platbrood, G.; Wilputte-Steinert, L. J. Mol. Catal. 1975/76, 1, 265-273. Fischler, I.; Budzwait, M.; Koerner von Gustorf, E. A. J. Organomet. Chem. 1976, 105, 325-330.
29. Gerhartz, W.; Grevels, F.-W.; Klotzbücher, W. E.; Koerner von Gustorf, E. A.; Perutz, R. N. Z. Naturforsch. 1984, 40B, 518-523.
30. Jackson, S. A.; Hodges, P. M.; Poliakoff, M.; Turner, J. J.; Grevels, F.-W. J. Am. Chem. Soc. 1990, 112, 1221-1233. Hodges, P. M.; Jackson, S. A.; Jacke, J.; Poliakoff, M.; Turner, J. J.; Grevels, F.-W. J. Am. Chem. Soc. 1990, 112, 1234-1244.
31. Jackson, S. A.; Hodges, P. M.; Poliakoff, M.; Turner, J. J.; Grevels, F.-W. J. Am. Chem. Soc. 1990, 112, 1221-1233. Hodges, P. M.; Jackson, S. A.; Jacke, J.; Poliakoff, M.; Turner, J. J.; Grevels, F.-W. J. Am. Chem. Soc. 1990, 112, 1234-1244.
32. Thomas, A.; Haake, M.; Grevels, F.-W.; Bargon, J. Angew. Chem. 1994, 106, 820-822; Angew. Chem., Int. Ed. Engl. 1994, 33, 755-757.
33. Thomas, A.; Haake, M.; Grevels, F.-W.; Bargon, J. Angew. Chem. 1994, 106, 820-822; Angew. Chem., Int. Ed. Engl. 1994, 33, 755-757.
34. Schubert, U. Adv. Organomet. Chem. 1990, 30, 151-187. Qjima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1990, 9, 3127-3133.
35. Schubert, U. Adv. Organomet. Chem. 1990, 30, 151-187. Qjima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1990, 9, 3127-3133.
36. Luo, X.-L.; Kubas, G. J.; Bryan, J. C.; Burns, C. J.; Unkefer, C. J. J. Am. Chem. Soc. 1994, 116, 10312-10313. Luo, X.-L.; Kubas, G. J.; Burns, C. J.; Bryan, J. C.; Unkefer, C. J. J. Am. Chem. Soc. 1995, 117, 1159-1160.
37. Luo, X.-L.; Kubas, G. J.; Bryan, J. C.; Burns, C. J.; Unkefer, C. J. J. Am. Chem. Soc. 1994, 116, 10312-10313. Luo, X.-L.; Kubas, G. J.; Burns, C. J.; Bryan, J. C.; Unkefer, C. J. J. Am. Chem. Soc. 1995, 117, 1159-1160.
38. Burkey, T. J. J. Am. Chem. Soc. 1990, 112, 8329-8333.
39. Zhang, S.; Dobson, G. R.; Brown, T. L. J. Am. Chem. Soc. 1991, 113, 6908-6916.
40. Chmielewski, D.; Grevels, F.-W.; Jacke, J.; Schaffner, K. Angew. Chem. 1991, 103, 1361-1363; Angew. Chem., Int. Ed. Engl. 1991, 30, 1343-1345.
41. Chmielewski, D.; Grevels, F.-W.; Jacke, J.; Schaffner, K. Angew. Chem. 1991, 103, 1361-1363; Angew. Chem., Int. Ed. Engl. 1991, 30, 1343-1345.
42. Jacke, J. Doctoral Dissertation, Universität Duisburg, Germany, 1989. Chmielewski, D. Doctoral Dissertation, Universität Duisburg, Germany, 1992.
43. Jacke, J. Doctoral Dissertation, Universität Duisburg, Germany, 1989. Chmielewski, D. Doctoral Dissertation, Universität Duisburg, Germany, 1992.
44. The extended Hückel program in the program package "HyperChem Version 3.0" (Autodesk Inc., 1992) was used to calculate the MO coefficients in the LUMO of the conjugated diene π systems. 1,3-Butadiene (1): C-1 (-0.651 37), C-2 (0.458 04), C-3 (0.458 04), C-4 (-0.651 37). 1,3-Pentadiene (2): C-1 (-0.644 47), C-2 (0.478 71), C-3 (0.412 30), C-4 (-0.663 91). 2-Methyl-1,3-butadiene (4): C-1 (-0.622 25), C-2 (0.449 77), C-3 (0.448 90), C-4 (-0.665 82). 2-Methyl-1,3-pentadiene (5): C-1 (-0.614 31), C-2 (0.469 31), C-3 (0.434 32), C-4 (-0.679 21).
45. Grevels, F.-W.; Reuvers, J. G. A.; Takats, J. Inorg. Synth. 1986, 24, 176-180.
46. West, R. J. Am. Chem. Soc. 1954, 76, 6012-6014.
47. The authors wish to thank Dr. T. Savasci of PETKIM Refinery, Kocaeli, Turkey, for the supply of 1,3-butadiene.
48. The authors wish to thank Dipl.-Ing. H. Bandmann (Universität Essen-GHS, Institut für Organische Chemie) for recording the 1D-INADEQUATE spectra.