Nickel-catalyzed reaction of highly fluorinated epoxides with halogens

Journal of the American Chemical Society

Volumn 118, Issue 34, 1996, Pages 8140-8141

  Yang, Zhen Yu ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOHALOGEN DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029832450     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961408s     Document Type: Article

References (54)

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16. 2 precursor: (a) Sargeant, P. B.; Krespan, C. G. J. Am Chem. Soc. 1969, 91, 415. (b) Sargeant, P. B. J. Org. Chem. 1970, 35, 678. (c) Chepik, S. D.; Petrov, V. A.: Galakhov, M. V.; Belen'kii, G. G.; Mysov, E. I.; German, L. S. Izv. Akad. Nauk SSSR, Seri. Khim. 1990, 8, 1844. (d) Millauer, H.; Schwertfeger, W.; Siegemund, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 161.
17. 2 precursor: (a) Sargeant, P. B.; Krespan, C. G. J. Am Chem. Soc. 1969, 91, 415. (b) Sargeant, P. B. J. Org. Chem. 1970, 35, 678. (c) Chepik, S. D.; Petrov, V. A.: Galakhov, M. V.; Belen'kii, G. G.; Mysov, E. I.; German, L. S. Izv. Akad. Nauk SSSR, Seri. Khim. 1990, 8, 1844. (d) Millauer, H.; Schwertfeger, W.; Siegemund, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 161.
18. 2 precursor: (a) Sargeant, P. B.; Krespan, C. G. J. Am Chem. Soc. 1969, 91, 415. (b) Sargeant, P. B. J. Org. Chem. 1970, 35, 678. (c) Chepik, S. D.; Petrov, V. A.: Galakhov, M. V.; Belen'kii, G. G.; Mysov, E. I.; German, L. S. Izv. Akad. Nauk SSSR, Seri. Khim. 1990, 8, 1844. (d) Millauer, H.; Schwertfeger, W.; Siegemund, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 161.
19. 2 precursor: (a) Sargeant, P. B.; Krespan, C. G. J. Am Chem. Soc. 1969, 91, 415. (b) Sargeant, P. B. J. Org. Chem. 1970, 35, 678. (c) Chepik, S. D.; Petrov, V. A.: Galakhov, M. V.; Belen'kii, G. G.; Mysov, E. I.; German, L. S. Izv. Akad. Nauk SSSR, Seri. Khim. 1990, 8, 1844. (d) Millauer, H.; Schwertfeger, W.; Siegemund, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 161.
20. (a) John, E. O.; Kirchmeier, R. L.; Shreeve, J. M. Inorg. Chem. 1992, 31, 329.
21. 2. In a glass tube, no yield was improved.
22. New Hydrogenation Catalysts: Urushibara Catalysts; Hata, K.; John Wiley & Son, Inc.: New York, 1972; pp 29-60.
23. 2I in a ratio of 39.3:1:3 (GC area).
24. 2 303.8057; found 303.8065.
25. 2 is too volatile to be isolated.
26. 2 as determined by powder X-ray diffraction. The X-ray diffraction pattern of this mixture is almost identical to that of recovered catalyst.
27. Ni(I) complexes: (a) Heimbach, P. Angew. Chem., Int. Edi. Engl. 1964, 3, 648. (b) Nilges, M. J.; Barefield, E. K.; Belford, R. L.; Davis, P. H. J. Am. Chem. Soc. 1977, 99, 755. (c) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. (d) Ratliff, K. S.; Broeker. G. K.; Fanwick, P. E.; Kubiak, C. P. Angew. Chem. 1990, 102, 405. (e) Morgenstern, D. A.; Wittrig, R. E.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1993, 115, 6470. (f) Cai, F. X.; Lepetit, C.; Kermarec, M.; Olivier, D. J. Mol. Catal. 1987, 43, 93. (g) Sibille, S.; Coulombeix, J.; Perichon, J.; Fuchs, J. Mortreux, A.; Petit, F. J. Mol. Catal. 1985, 32, 239. (h) Bonneviot, L.; Olivier, D.; Che. M. J. Mol. Catal. 1983, 21, 415.
28. Ni(I) complexes: (a) Heimbach, P. Angew. Chem., Int. Edi. Engl. 1964, 3, 648. (b) Nilges, M. J.; Barefield, E. K.; Belford, R. L.; Davis, P. H. J. Am. Chem. Soc. 1977, 99, 755. (c) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. (d) Ratliff, K. S.; Broeker. G. K.; Fanwick, P. E.; Kubiak, C. P. Angew. Chem. 1990, 102, 405. (e) Morgenstern, D. A.; Wittrig, R. E.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1993, 115, 6470. (f) Cai, F. X.; Lepetit, C.; Kermarec, M.; Olivier, D. J. Mol. Catal. 1987, 43, 93. (g) Sibille, S.; Coulombeix, J.; Perichon, J.; Fuchs, J. Mortreux, A.; Petit, F. J. Mol. Catal. 1985, 32, 239. (h) Bonneviot, L.; Olivier, D.; Che. M. J. Mol. Catal. 1983, 21, 415.
29. Ni(I) complexes: (a) Heimbach, P. Angew. Chem., Int. Edi. Engl. 1964, 3, 648. (b) Nilges, M. J.; Barefield, E. K.; Belford, R. L.; Davis, P. H. J. Am. Chem. Soc. 1977, 99, 755. (c) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. (d) Ratliff, K. S.; Broeker. G. K.; Fanwick, P. E.; Kubiak, C. P. Angew. Chem. 1990, 102, 405. (e) Morgenstern, D. A.; Wittrig, R. E.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1993, 115, 6470. (f) Cai, F. X.; Lepetit, C.; Kermarec, M.; Olivier, D. J. Mol. Catal. 1987, 43, 93. (g) Sibille, S.; Coulombeix, J.; Perichon, J.; Fuchs, J. Mortreux, A.; Petit, F. J. Mol. Catal. 1985, 32, 239. (h) Bonneviot, L.; Olivier, D.; Che. M. J. Mol. Catal. 1983, 21, 415.
30. Ni(I) complexes: (a) Heimbach, P. Angew. Chem., Int. Edi. Engl. 1964, 3, 648. (b) Nilges, M. J.; Barefield, E. K.; Belford, R. L.; Davis, P. H. J. Am. Chem. Soc. 1977, 99, 755. (c) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. (d) Ratliff, K. S.; Broeker. G. K.; Fanwick, P. E.; Kubiak, C. P. Angew. Chem. 1990, 102, 405. (e) Morgenstern, D. A.; Wittrig, R. E.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1993, 115, 6470. (f) Cai, F. X.; Lepetit, C.; Kermarec, M.; Olivier, D. J. Mol. Catal. 1987, 43, 93. (g) Sibille, S.; Coulombeix, J.; Perichon, J.; Fuchs, J. Mortreux, A.; Petit, F. J. Mol. Catal. 1985, 32, 239. (h) Bonneviot, L.; Olivier, D.; Che. M. J. Mol. Catal. 1983, 21, 415.
31. Ni(I) complexes: (a) Heimbach, P. Angew. Chem., Int. Edi. Engl. 1964, 3, 648. (b) Nilges, M. J.; Barefield, E. K.; Belford, R. L.; Davis, P. H. J. Am. Chem. Soc. 1977, 99, 755. (c) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. (d) Ratliff, K. S.; Broeker. G. K.; Fanwick, P. E.; Kubiak, C. P. Angew. Chem. 1990, 102, 405. (e) Morgenstern, D. A.; Wittrig, R. E.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1993, 115, 6470. (f) Cai, F. X.; Lepetit, C.; Kermarec, M.; Olivier, D. J. Mol. Catal. 1987, 43, 93. (g) Sibille, S.; Coulombeix, J.; Perichon, J.; Fuchs, J. Mortreux, A.; Petit, F. J. Mol. Catal. 1985, 32, 239. (h) Bonneviot, L.; Olivier, D.; Che. M. J. Mol. Catal. 1983, 21, 415.
32. Ni(I) complexes: (a) Heimbach, P. Angew. Chem., Int. Edi. Engl. 1964, 3, 648. (b) Nilges, M. J.; Barefield, E. K.; Belford, R. L.; Davis, P. H. J. Am. Chem. Soc. 1977, 99, 755. (c) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. (d) Ratliff, K. S.; Broeker. G. K.; Fanwick, P. E.; Kubiak, C. P. Angew. Chem. 1990, 102, 405. (e) Morgenstern, D. A.; Wittrig, R. E.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1993, 115, 6470. (f) Cai, F. X.; Lepetit, C.; Kermarec, M.; Olivier, D. J. Mol. Catal. 1987, 43, 93. (g) Sibille, S.; Coulombeix, J.; Perichon, J.; Fuchs, J. Mortreux, A.; Petit, F. J. Mol. Catal. 1985, 32, 239. (h) Bonneviot, L.; Olivier, D.; Che. M. J. Mol. Catal. 1983, 21, 415.
33. Ni(I) complexes: (a) Heimbach, P. Angew. Chem., Int. Edi. Engl. 1964, 3, 648. (b) Nilges, M. J.; Barefield, E. K.; Belford, R. L.; Davis, P. H. J. Am. Chem. Soc. 1977, 99, 755. (c) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. (d) Ratliff, K. S.; Broeker. G. K.; Fanwick, P. E.; Kubiak, C. P. Angew. Chem. 1990, 102, 405. (e) Morgenstern, D. A.; Wittrig, R. E.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1993, 115, 6470. (f) Cai, F. X.; Lepetit, C.; Kermarec, M.; Olivier, D. J. Mol. Catal. 1987, 43, 93. (g) Sibille, S.; Coulombeix, J.; Perichon, J.; Fuchs, J. Mortreux, A.; Petit, F. J. Mol. Catal. 1985, 32, 239. (h) Bonneviot, L.; Olivier, D.; Che. M. J. Mol. Catal. 1983, 21, 415.
34. Ni(I) complexes: (a) Heimbach, P. Angew. Chem., Int. Edi. Engl. 1964, 3, 648. (b) Nilges, M. J.; Barefield, E. K.; Belford, R. L.; Davis, P. H. J. Am. Chem. Soc. 1977, 99, 755. (c) Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319. (d) Ratliff, K. S.; Broeker. G. K.; Fanwick, P. E.; Kubiak, C. P. Angew. Chem. 1990, 102, 405. (e) Morgenstern, D. A.; Wittrig, R. E.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1993, 115, 6470. (f) Cai, F. X.; Lepetit, C.; Kermarec, M.; Olivier, D. J. Mol. Catal. 1987, 43, 93. (g) Sibille, S.; Coulombeix, J.; Perichon, J.; Fuchs, J. Mortreux, A.; Petit, F. J. Mol. Catal. 1985, 32, 239. (h) Bonneviot, L.; Olivier, D.; Che. M. J. Mol. Catal. 1983, 21, 415.
35. 2 was observed at or below 250 °C, see: Ginzburg, V. I.; Kabakova, O. I. Zashch. Met. 1969, 5, 672.
36. 2 was observed at or below 250 °C, see: Ginzburg, V. I.; Kabakova, O. I. Zashch. Met. 1969, 5, 672.
37. The oxidative additions of hydrocarbon epoxides to nickel complexes in homogeneous solution and to Ni ion beams in the gas phase were proposed. The oxidative addition product in gas phase decomposes to give Ni carbene complex, see: (a) De Pasquale, R. J. J. Chem. Soc., Chem. Commun. 1973, 157. (b) Halle, L. F.; Armentrout, P. B.; Beauchamp, J. L. Organometallics, 1983, 2, 1829. For carbon-oxygen bond activation of epoxides by other transition metal complexes, see: (c) Walter, D. Cood. Chem. Rev. 1987, 79, 135. (d) Backvall, J. E.; Karlsson, O.; Ljunggren, S. O. Tetrahedron Lett. 1980, 21, 4985. (e) Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. (f) Aye, K.-T.; Gelmini. L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464. Intermediate B may also be possible in this reaction since the C-O bond is stronger than the C-C bond in perfluoroethers, see: Molecular Structure and Energetics; Liebman, J. F., Green berg. A., Eds.; VCH Publishers: Deerfield Beach, FL, 1986; Vol. 3, Chapter 4.
38. The oxidative additions of hydrocarbon epoxides to nickel complexes in homogeneous solution and to Ni ion beams in the gas phase were proposed. The oxidative addition product in gas phase decomposes to give Ni carbene complex, see: (a) De Pasquale, R. J. J. Chem. Soc., Chem. Commun. 1973, 157. (b) Halle, L. F.; Armentrout, P. B.; Beauchamp, J. L. Organometallics, 1983, 2, 1829. For carbon-oxygen bond activation of epoxides by other transition metal complexes, see: (c) Walter, D. Cood. Chem. Rev. 1987, 79, 135. (d) Backvall, J. E.; Karlsson, O.; Ljunggren, S. O. Tetrahedron Lett. 1980, 21, 4985. (e) Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. (f) Aye, K.-T.; Gelmini. L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464. Intermediate B may also be possible in this reaction since the C-O bond is stronger than the C-C bond in perfluoroethers, see: Molecular Structure and Energetics; Liebman, J. F., Green berg. A., Eds.; VCH Publishers: Deerfield Beach, FL, 1986; Vol. 3, Chapter 4.
39. The oxidative additions of hydrocarbon epoxides to nickel complexes in homogeneous solution and to Ni ion beams in the gas phase were proposed. The oxidative addition product in gas phase decomposes to give Ni carbene complex, see: (a) De Pasquale, R. J. J. Chem. Soc., Chem. Commun. 1973, 157. (b) Halle, L. F.; Armentrout, P. B.; Beauchamp, J. L. Organometallics, 1983, 2, 1829. For carbon-oxygen bond activation of epoxides by other transition metal complexes, see: (c) Walter, D. Cood. Chem. Rev. 1987, 79, 135. (d) Backvall, J. E.; Karlsson, O.; Ljunggren, S. O. Tetrahedron Lett. 1980, 21, 4985. (e) Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. (f) Aye, K.-T.; Gelmini. L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464. Intermediate B may also be possible in this reaction since the C-O bond is stronger than the C-C bond in perfluoroethers, see: Molecular Structure and Energetics; Liebman, J. F., Green berg. A., Eds.; VCH Publishers: Deerfield Beach, FL, 1986; Vol. 3, Chapter 4.
40. The oxidative additions of hydrocarbon epoxides to nickel complexes in homogeneous solution and to Ni ion beams in the gas phase were proposed. The oxidative addition product in gas phase decomposes to give Ni carbene complex, see: (a) De Pasquale, R. J. J. Chem. Soc., Chem. Commun. 1973, 157. (b) Halle, L. F.; Armentrout, P. B.; Beauchamp, J. L. Organometallics, 1983, 2, 1829. For carbon-oxygen bond activation of epoxides by other transition metal complexes, see: (c) Walter, D. Cood. Chem. Rev. 1987, 79, 135. (d) Backvall, J. E.; Karlsson, O.; Ljunggren, S. O. Tetrahedron Lett. 1980, 21, 4985. (e) Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. (f) Aye, K.-T.; Gelmini. L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464. Intermediate B may also be possible in this reaction since the C-O bond is stronger than the C-C bond in perfluoroethers, see: Molecular Structure and Energetics; Liebman, J. F., Green berg. A., Eds.; VCH Publishers: Deerfield Beach, FL, 1986; Vol. 3, Chapter 4.
41. The oxidative additions of hydrocarbon epoxides to nickel complexes in homogeneous solution and to Ni ion beams in the gas phase were proposed. The oxidative addition product in gas phase decomposes to give Ni carbene complex, see: (a) De Pasquale, R. J. J. Chem. Soc., Chem. Commun. 1973, 157. (b) Halle, L. F.; Armentrout, P. B.; Beauchamp, J. L. Organometallics, 1983, 2, 1829. For carbon-oxygen bond activation of epoxides by other transition metal complexes, see: (c) Walter, D. Cood. Chem. Rev. 1987, 79, 135. (d) Backvall, J. E.; Karlsson, O.; Ljunggren, S. O. Tetrahedron Lett. 1980, 21, 4985. (e) Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. (f) Aye, K.-T.; Gelmini. L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464. Intermediate B may also be possible in this reaction since the C-O bond is stronger than the C-C bond in perfluoroethers, see: Molecular Structure and Energetics; Liebman, J. F., Green berg. A., Eds.; VCH Publishers: Deerfield Beach, FL, 1986; Vol. 3, Chapter 4.
42. The oxidative additions of hydrocarbon epoxides to nickel complexes in homogeneous solution and to Ni ion beams in the gas phase were proposed. The oxidative addition product in gas phase decomposes to give Ni carbene complex, see: (a) De Pasquale, R. J. J. Chem. Soc., Chem. Commun. 1973, 157. (b) Halle, L. F.; Armentrout, P. B.; Beauchamp, J. L. Organometallics, 1983, 2, 1829. For carbon-oxygen bond activation of epoxides by other transition metal complexes, see: (c) Walter, D. Cood. Chem. Rev. 1987, 79, 135. (d) Backvall, J. E.; Karlsson, O.; Ljunggren, S. O. Tetrahedron Lett. 1980, 21, 4985. (e) Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. (f) Aye, K.-T.; Gelmini. L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464. Intermediate B may also be possible in this reaction since the C-O bond is stronger than the C-C bond in perfluoroethers, see: Molecular Structure and Energetics; Liebman, J. F., Green berg. A., Eds.; VCH Publishers: Deerfield Beach, FL, 1986; Vol. 3, Chapter 4.
43. The oxidative additions of hydrocarbon epoxides to nickel complexes in homogeneous solution and to Ni ion beams in the gas phase were proposed. The oxidative addition product in gas phase decomposes to give Ni carbene complex, see: (a) De Pasquale, R. J. J. Chem. Soc., Chem. Commun. 1973, 157. (b) Halle, L. F.; Armentrout, P. B.; Beauchamp, J. L. Organometallics, 1983, 2, 1829. For carbon-oxygen bond activation of epoxides by other transition metal complexes, see: (c) Walter, D. Cood. Chem. Rev. 1987, 79, 135. (d) Backvall, J. E.; Karlsson, O.; Ljunggren, S. O. Tetrahedron Lett. 1980, 21, 4985. (e) Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123. (f) Aye, K.-T.; Gelmini. L.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. J. Am. Chem. Soc. 1990, 112, 2464. Intermediate B may also be possible in this reaction since the C-O bond is stronger than the C-C bond in perfluoroethers, see: Molecular Structure and Energetics; Liebman, J. F., Green berg. A., Eds.; VCH Publishers: Deerfield Beach, FL, 1986; Vol. 3, Chapter 4.
44. 3P at -78 °C. See: Klabunde, K. J. Angew. Chem., Int. Ed. Engl. 1975, 14, 287. We believe that the intermediates A and/or B are highly reactive.
45. 3P at -78 °C. See: Klabunde, K. J. Angew. Chem., Int. Ed. Engl. 1975, 14, 287. We believe that the intermediates A and/or B are highly reactive.
46. 2. See: Su, D. B.; Duan, J. X.: Chen. Q. C. J. Chem. Soc., Chem. Commun. 1992, 807.
47. 2 complexes, see: (d) Clark, G. R.; Hoskins, S. V.; Jones, T. C.; Roper, W. R. J. Chem. Soc., Chem. Commun. 1983, 719. (e) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121.
48. 2 complexes, see: (d) Clark, G. R.; Hoskins, S. V.; Jones, T. C.; Roper, W. R. J. Chem. Soc., Chem. Commun. 1983, 719. (e) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121.
49. 2 complexes, see: (d) Clark, G. R.; Hoskins, S. V.; Jones, T. C.; Roper, W. R. J. Chem. Soc., Chem. Commun. 1983, 719. (e) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121.
50. 2 complexes, see: (d) Clark, G. R.; Hoskins, S. V.; Jones, T. C.; Roper, W. R. J. Chem. Soc., Chem. Commun. 1983, 719. (e) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121.
51. 2 complexes, see: (d) Clark, G. R.; Hoskins, S. V.; Jones, T. C.; Roper, W. R. J. Chem. Soc., Chem. Commun. 1983, 719. (e) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121.
52. 2 complexes, see: (d) Clark, G. R.; Hoskins, S. V.; Jones, T. C.; Roper, W. R. J. Chem. Soc., Chem. Commun. 1983, 719. (e) Gallop, M. A.; Roper, W. R. Adv. Organomet. Chem. 1986, 25, 121.
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54. Elsheimer, S.; Dolbier, W. R.; Murla, M. J. Org. Chem. 1984, 49, 205