The porphyrinogen-porphyrin relationship: The discovery of artificial porphyrins

Chemical Communications

Volumn , Issue 11, 1996, Pages 1257-1263

  Floriani, Carlo ^a,b,c  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITY OF PISA   (Italy)

^c Department of Chemistry ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002197973     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001257     Document Type: Article

References (65)

1. Porphyrins and Metalloporphyrins, ed. K. M. Smith, Elsevier, Amsterdam, The Netherlands, 1975; The Porphyrins, ed. D. Dolphin, Academic, New York, 1978; T. Mashiko and D. Dolphin, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon, Oxford, 1987, vol. 2, ch. 21.1, p. 855; J. B. Kim, A. D. Adler and R. F. Longo, in The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 1, part A, p. 85; D. Mauzerall, The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 2, p. 91; J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827; J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828; Biosynthesis of Tetrapyrroles, ed. P. M. Jordan, Elsevier, New York, 1991.
2. Porphyrins and Metalloporphyrins, ed. K. M. Smith, Elsevier, Amsterdam, The Netherlands, 1975; The Porphyrins, ed. D. Dolphin, Academic, New York, 1978; T. Mashiko and D. Dolphin, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon, Oxford, 1987, vol. 2, ch. 21.1, p. 855; J. B. Kim, A. D. Adler and R. F. Longo, in The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 1, part A, p. 85; D. Mauzerall, The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 2, p. 91; J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827; J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828; Biosynthesis of Tetrapyrroles, ed. P. M. Jordan, Elsevier, New York, 1991.
3. Porphyrins and Metalloporphyrins, ed. K. M. Smith, Elsevier, Amsterdam, The Netherlands, 1975; The Porphyrins, ed. D. Dolphin, Academic, New York, 1978; T. Mashiko and D. Dolphin, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon, Oxford, 1987, vol. 2, ch. 21.1, p. 855; J. B. Kim, A. D. Adler and R. F. Longo, in The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 1, part A, p. 85; D. Mauzerall, The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 2, p. 91; J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827; J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828; Biosynthesis of Tetrapyrroles, ed. P. M. Jordan, Elsevier, New York, 1991.
4. Porphyrins and Metalloporphyrins, ed. K. M. Smith, Elsevier, Amsterdam, The Netherlands, 1975; The Porphyrins, ed. D. Dolphin, Academic, New York, 1978; T. Mashiko and D. Dolphin, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon, Oxford, 1987, vol. 2, ch. 21.1, p. 855; J. B. Kim, A. D. Adler and R. F. Longo, in The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 1, part A, p. 85; D. Mauzerall, The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 2, p. 91; J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827; J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828; Biosynthesis of Tetrapyrroles, ed. P. M. Jordan, Elsevier, New York, 1991.
5. Porphyrins and Metalloporphyrins, ed. K. M. Smith, Elsevier, Amsterdam, The Netherlands, 1975; The Porphyrins, ed. D. Dolphin, Academic, New York, 1978; T. Mashiko and D. Dolphin, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon, Oxford, 1987, vol. 2, ch. 21.1, p. 855; J. B. Kim, A. D. Adler and R. F. Longo, in The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 1, part A, p. 85; D. Mauzerall, The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 2, p. 91; J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827; J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828; Biosynthesis of Tetrapyrroles, ed. P. M. Jordan, Elsevier, New York, 1991.
6. Porphyrins and Metalloporphyrins, ed. K. M. Smith, Elsevier, Amsterdam, The Netherlands, 1975; The Porphyrins, ed. D. Dolphin, Academic, New York, 1978; T. Mashiko and D. Dolphin, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon, Oxford, 1987, vol. 2, ch. 21.1, p. 855; J. B. Kim, A. D. Adler and R. F. Longo, in The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 1, part A, p. 85; D. Mauzerall, The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 2, p. 91; J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827; J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828; Biosynthesis of Tetrapyrroles, ed. P. M. Jordan, Elsevier, New York, 1991.
7. Porphyrins and Metalloporphyrins, ed. K. M. Smith, Elsevier, Amsterdam, The Netherlands, 1975; The Porphyrins, ed. D. Dolphin, Academic, New York, 1978; T. Mashiko and D. Dolphin, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon, Oxford, 1987, vol. 2, ch. 21.1, p. 855; J. B. Kim, A. D. Adler and R. F. Longo, in The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 1, part A, p. 85; D. Mauzerall, The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 2, p. 91; J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827; J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828; Biosynthesis of Tetrapyrroles, ed. P. M. Jordan, Elsevier, New York, 1991.
8. Porphyrins and Metalloporphyrins, ed. K. M. Smith, Elsevier, Amsterdam, The Netherlands, 1975; The Porphyrins, ed. D. Dolphin, Academic, New York, 1978; T. Mashiko and D. Dolphin, in Comprehensive Coordination Chemistry, ed. G. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon, Oxford, 1987, vol. 2, ch. 21.1, p. 855; J. B. Kim, A. D. Adler and R. F. Longo, in The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 1, part A, p. 85; D. Mauzerall, The Porphyrins, ed. D. Dolphin, Academic, New York, 1978, vol. 2, p. 91; J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827; J. S. Lindsey and R. W. Wagner, J. Org. Chem., 1989, 54, 828; Biosynthesis of Tetrapyrroles, ed. P. M. Jordan, Elsevier, New York, 1991.
9. A. Baeyer, Chem. Ber., 1886, 19, 2184.
10. H. Fischer and H. Orth, Die Chemie des Pyrrols, Akademische Verlagsgesellschaft, Leipzig, Germany, 1934, p. 20; M. Dennstedt and J. Zimmermann, Chem. Ber., 1887, 20, 850, 2449; 1888, 21, 1478; D. Dennstedt, Chem. Ber., 1890, 23, 1370; V. V. Chelintzev and B. V. Tronov, J. Russ. Phys. Chem. Soc., 1916, 48, 105, 127; Th. Sabalitschka and H. Haase, Arch. Pharm., 1928, 226, 484; P. Rothemund and C. L. Gage, J. Am. Chem. Soc., 1955, 77, 3340.
11. H. Fischer and H. Orth, Die Chemie des Pyrrols, Akademische Verlagsgesellschaft, Leipzig, Germany, 1934, p. 20; M. Dennstedt and J. Zimmermann, Chem. Ber., 1887, 20, 850, 2449; 1888, 21, 1478; D. Dennstedt, Chem. Ber., 1890, 23, 1370; V. V. Chelintzev and B. V. Tronov, J. Russ. Phys. Chem. Soc., 1916, 48, 105, 127; Th. Sabalitschka and H. Haase, Arch. Pharm., 1928, 226, 484; P. Rothemund and C. L. Gage, J. Am. Chem. Soc., 1955, 77, 3340.
12. H. Fischer and H. Orth, Die Chemie des Pyrrols, Akademische Verlagsgesellschaft, Leipzig, Germany, 1934, p. 20; M. Dennstedt and J. Zimmermann, Chem. Ber., 1887, 20, 850, 2449; 1888, 21, 1478; D. Dennstedt, Chem. Ber., 1890, 23, 1370; V. V. Chelintzev and B. V. Tronov, J. Russ. Phys. Chem. Soc., 1916, 48, 105, 127; Th. Sabalitschka and H. Haase, Arch. Pharm., 1928, 226, 484; P. Rothemund and C. L. Gage, J. Am. Chem. Soc., 1955, 77, 3340.
13. H. Fischer and H. Orth, Die Chemie des Pyrrols, Akademische Verlagsgesellschaft, Leipzig, Germany, 1934, p. 20; M. Dennstedt and J. Zimmermann, Chem. Ber., 1887, 20, 850, 2449; 1888, 21, 1478; D. Dennstedt, Chem. Ber., 1890, 23, 1370; V. V. Chelintzev and B. V. Tronov, J. Russ. Phys. Chem. Soc., 1916, 48, 105, 127; Th. Sabalitschka and H. Haase, Arch. Pharm., 1928, 226, 484; P. Rothemund and C. L. Gage, J. Am. Chem. Soc., 1955, 77, 3340.
14. H. Fischer and H. Orth, Die Chemie des Pyrrols, Akademische Verlagsgesellschaft, Leipzig, Germany, 1934, p. 20; M. Dennstedt and J. Zimmermann, Chem. Ber., 1887, 20, 850, 2449; 1888, 21, 1478; D. Dennstedt, Chem. Ber., 1890, 23, 1370; V. V. Chelintzev and B. V. Tronov, J. Russ. Phys. Chem. Soc., 1916, 48, 105, 127; Th. Sabalitschka and H. Haase, Arch. Pharm., 1928, 226, 484; P. Rothemund and C. L. Gage, J. Am. Chem. Soc., 1955, 77, 3340.
15. H. Fischer and H. Orth, Die Chemie des Pyrrols, Akademische Verlagsgesellschaft, Leipzig, Germany, 1934, p. 20; M. Dennstedt and J. Zimmermann, Chem. Ber., 1887, 20, 850, 2449; 1888, 21, 1478; D. Dennstedt, Chem. Ber., 1890, 23, 1370; V. V. Chelintzev and B. V. Tronov, J. Russ. Phys. Chem. Soc., 1916, 48, 105, 127; Th. Sabalitschka and H. Haase, Arch. Pharm., 1928, 226, 484; P. Rothemund and C. L. Gage, J. Am. Chem. Soc., 1955, 77, 3340.
16. H. Fischer and H. Orth, Die Chemie des Pyrrols, Akademische Verlagsgesellschaft, Leipzig, Germany, 1934, p. 20; M. Dennstedt and J. Zimmermann, Chem. Ber., 1887, 20, 850, 2449; 1888, 21, 1478; D. Dennstedt, Chem. Ber., 1890, 23, 1370; V. V. Chelintzev and B. V. Tronov, J. Russ. Phys. Chem. Soc., 1916, 48, 105, 127; Th. Sabalitschka and H. Haase, Arch. Pharm., 1928, 226, 484; P. Rothemund and C. L. Gage, J. Am. Chem. Soc., 1955, 77, 3340.
17. (a) J. Jubb, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1992, 114, 6571;
18. (b) U. Piarulli, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Chem. Soc., Chem. Commun., 1994, 895;
19. (c) S. De Angelis, E. Solari, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1994, 116, 5691;
20. (d) S. De Angelis, E. Solari, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1994, 116, 5702;
21. (e) C. Floriani, Transition Metals in Supramolecular Chemistry, ed. L. Fabbrizzi and A. Poggi, Nato ASI Series, Kluwer, Dordrecht, 1994, vol. 448, pp. 191-209.
22. C. Floriani, Pure Appl. Chem., 1996, 68, 1.
23. (a) D. Jacoby, S. Isoz, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1995, 117, 2805;
24. (b) S. Isoz, C. Floriani, K. Schenk, A. Chiesi-Villa and C. Rizzoli, Organometallics, 1996, 15, 337.
25. D. Jacoby, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1993, 115, 7025; D. Jacoby, S. Isoz, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1995, 117, 2793; C. Floriani, in Stereoselective Reactions of Metal-Activated Molecules, ed. H. Werner and J. Sundermeyer, Vieweg, Wiesbaden, 1995, 97.
26. D. Jacoby, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1993, 115, 7025; D. Jacoby, S. Isoz, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1995, 117, 2793; C. Floriani, in Stereoselective Reactions of Metal-Activated Molecules, ed. H. Werner and J. Sundermeyer, Vieweg, Wiesbaden, 1995, 97.
27. D. Jacoby, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1993, 115, 7025; D. Jacoby, S. Isoz, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1995, 117, 2793; C. Floriani, in Stereoselective Reactions of Metal-Activated Molecules, ed. H. Werner and J. Sundermeyer, Vieweg, Wiesbaden, 1995, 97.
28. B. von Maltzan, Angew. Chem., Int. Ed. Engl., 1982, 21, 785.
29. C. D. Gutsche, Calixarenes, The Royal Society of Chemistry, Cambridge, UK, 1989; Calixarenes, A Versatile Class of Macrocyclic Compounds, ed. J. Vicens and V. Böhmer, Kluwer, Dordrecht, The Netherlands, 1991.
30. C. D. Gutsche, Calixarenes, The Royal Society of Chemistry, Cambridge, UK, 1989; Calixarenes, A Versatile Class of Macrocyclic Compounds, ed. J. Vicens and V. Böhmer, Kluwer, Dordrecht, The Netherlands, 1991.
31. S. De Angelis, E. Solari, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Chem. Soc., Dalton Trans., 1994, 2467.
32. (a) D. Jacoby, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1993, 115, 3595;
33. (b) D. Jacoby, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Chem. Soc., Chem. Commun., 1991, 790;
34. (c) A. Rosa, M. Ricciardi, A. Sgamellotti and C. Floriani, J. Chem. Soc., Dalton Trans., 1993, 3759.
35. J. Jubb, D. Jacoby, C. Floriani, A. Chiesi-Villa and C. Rizzoli, Inorg. Chem., 1992, 31, 1306.
36. (a) S. De Angelis, E. Solari, C. Floriani, A. Chiesi-Villa and C. Rizzoli, Angew. Chem., Int. Ed. Engl., 1995, 34, 1092;
37. (b) D. Jacoby, S. Isoz, C. Floriani, K. Schenk, A. Chiesi-Villa and C. Rizzoli, Organometallics, 1995, 14, 4816;
38. (c) S. De Angelis, E. Solari, C. Floriani, A. Chiesi-Villa and C. Rizzoli, Organometallics, 1995, 14, 4505.
39. C. Floriani, unpublished work.
40. U. Piarulli, E. Solari, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., in the press.
41. For a general review on the homologation reaction of alcohols and related species, see: G. P. Chiusoli, G. Salerno and M. Foa, in Reactions of Coordinated Ligands, ed. P. S. Braterman, Plenum, New York, 1986, vol. 1, ch. 7; G. W. Parshall and S. D. Ittel, Homogeneous Catalysis, 2nd ed., Wiley, New York, 1992; H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation, Plenum, New York, 1991.
42. For a general review on the homologation reaction of alcohols and related species, see: G. P. Chiusoli, G. Salerno and M. Foa, in Reactions of Coordinated Ligands, ed. P. S. Braterman, Plenum, New York, 1986, vol. 1, ch. 7; G. W. Parshall and S. D. Ittel, Homogeneous Catalysis, 2nd ed., Wiley, New York, 1992; H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation, Plenum, New York, 1991.
43. For a general review on the homologation reaction of alcohols and related species, see: G. P. Chiusoli, G. Salerno and M. Foa, in Reactions of Coordinated Ligands, ed. P. S. Braterman, Plenum, New York, 1986, vol. 1, ch. 7; G. W. Parshall and S. D. Ittel, Homogeneous Catalysis, 2nd ed., Wiley, New York, 1992; H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation, Plenum, New York, 1991.
44. L. D. Durfee and I. P. Rothwell, Chem. Rev., 1988, 88, 1059; P. T. Wolczanski and J. E. Bercaw, Acc. Chem. Res., 1980, 13, 121; C. E. L. Headford and W. R. Roper, in Reactions of Coordinated Ligands, ed. P. S. Braterman, Plenum, New York, 1986, vol. 1, ch. 8; J. A. Labinger, Transition Metal Hydrides, ed. A. Dedieu, VCH, Weinheim, Germany, 1992.
45. L. D. Durfee and I. P. Rothwell, Chem. Rev., 1988, 88, 1059; P. T. Wolczanski and J. E. Bercaw, Acc. Chem. Res., 1980, 13, 121; C. E. L. Headford and W. R. Roper, in Reactions of Coordinated Ligands, ed. P. S. Braterman, Plenum, New York, 1986, vol. 1, ch. 8; J. A. Labinger, Transition Metal Hydrides, ed. A. Dedieu, VCH, Weinheim, Germany, 1992.
46. L. D. Durfee and I. P. Rothwell, Chem. Rev., 1988, 88, 1059; P. T. Wolczanski and J. E. Bercaw, Acc. Chem. Res., 1980, 13, 121; C. E. L. Headford and W. R. Roper, in Reactions of Coordinated Ligands, ed. P. S. Braterman, Plenum, New York, 1986, vol. 1, ch. 8; J. A. Labinger, Transition Metal Hydrides, ed. A. Dedieu, VCH, Weinheim, Germany, 1992.
47. L. D. Durfee and I. P. Rothwell, Chem. Rev., 1988, 88, 1059; P. T. Wolczanski and J. E. Bercaw, Acc. Chem. Res., 1980, 13, 121; C. E. L. Headford and W. R. Roper, in Reactions of Coordinated Ligands, ed. P. S. Braterman, Plenum, New York, 1986, vol. 1, ch. 8; J. A. Labinger, Transition Metal Hydrides, ed. A. Dedieu, VCH, Weinheim, Germany, 1992.
48. K. Tatsumi, A. Nakamura, P. Hofmann, P. Stauffert and R. Hoffmann, J. Am. Chem. Soc., 1985, 107, 4440; B. D. Martin, S. A. Matchett, J. R. Norton and O. P. Anderson, J. Am. Chem. Soc., 1985, 107, 7952; D. M. Roddick and J. E. Bercaw, Chem. Ber., 1989, 122, 1579; P. Hofmann, P. Stauffert, M. Frede and K. Tatsumi, Chem. Ber., 1989, 122, 1559; P. Hofmann, P. Stauffert, K. Tatsumi, A. Nakamura and R. Hoffmann, Organometallics, 1985, 4, 404; K. Tatsumi, A. Nakamura, P. Hofmann, R. Hoffmann, K. G. Moloy and T. J. Marks, J. Am. Chem. Soc., 1986, 108, 4467.
49. K. Tatsumi, A. Nakamura, P. Hofmann, P. Stauffert and R. Hoffmann, J. Am. Chem. Soc., 1985, 107, 4440; B. D. Martin, S. A. Matchett, J. R. Norton and O. P. Anderson, J. Am. Chem. Soc., 1985, 107, 7952; D. M. Roddick and J. E. Bercaw, Chem. Ber., 1989, 122, 1579; P. Hofmann, P. Stauffert, M. Frede and K. Tatsumi, Chem. Ber., 1989, 122, 1559; P. Hofmann, P. Stauffert, K. Tatsumi, A. Nakamura and R. Hoffmann, Organometallics, 1985, 4, 404; K. Tatsumi, A. Nakamura, P. Hofmann, R. Hoffmann, K. G. Moloy and T. J. Marks, J. Am. Chem. Soc., 1986, 108, 4467.
50. K. Tatsumi, A. Nakamura, P. Hofmann, P. Stauffert and R. Hoffmann, J. Am. Chem. Soc., 1985, 107, 4440; B. D. Martin, S. A. Matchett, J. R. Norton and O. P. Anderson, J. Am. Chem. Soc., 1985, 107, 7952; D. M. Roddick and J. E. Bercaw, Chem. Ber., 1989, 122, 1579; P. Hofmann, P. Stauffert, M. Frede and K. Tatsumi, Chem. Ber., 1989, 122, 1559; P. Hofmann, P. Stauffert, K. Tatsumi, A. Nakamura and R. Hoffmann, Organometallics, 1985, 4, 404; K. Tatsumi, A. Nakamura, P. Hofmann, R. Hoffmann, K. G. Moloy and T. J. Marks, J. Am. Chem. Soc., 1986, 108, 4467.
51. K. Tatsumi, A. Nakamura, P. Hofmann, P. Stauffert and R. Hoffmann, J. Am. Chem. Soc., 1985, 107, 4440; B. D. Martin, S. A. Matchett, J. R. Norton and O. P. Anderson, J. Am. Chem. Soc., 1985, 107, 7952; D. M. Roddick and J. E. Bercaw, Chem. Ber., 1989, 122, 1579; P. Hofmann, P. Stauffert, M. Frede and K. Tatsumi, Chem. Ber., 1989, 122, 1559; P. Hofmann, P. Stauffert, K. Tatsumi, A. Nakamura and R. Hoffmann, Organometallics, 1985, 4, 404; K. Tatsumi, A. Nakamura, P. Hofmann, R. Hoffmann, K. G. Moloy and T. J. Marks, J. Am. Chem. Soc., 1986, 108, 4467.
52. K. Tatsumi, A. Nakamura, P. Hofmann, P. Stauffert and R. Hoffmann, J. Am. Chem. Soc., 1985, 107, 4440; B. D. Martin, S. A. Matchett, J. R. Norton and O. P. Anderson, J. Am. Chem. Soc., 1985, 107, 7952; D. M. Roddick and J. E. Bercaw, Chem. Ber., 1989, 122, 1579; P. Hofmann, P. Stauffert, M. Frede and K. Tatsumi, Chem. Ber., 1989, 122, 1559; P. Hofmann, P. Stauffert, K. Tatsumi, A. Nakamura and R. Hoffmann, Organometallics, 1985, 4, 404; K. Tatsumi, A. Nakamura, P. Hofmann, R. Hoffmann, K. G. Moloy and T. J. Marks, J. Am. Chem. Soc., 1986, 108, 4467.
53. K. Tatsumi, A. Nakamura, P. Hofmann, P. Stauffert and R. Hoffmann, J. Am. Chem. Soc., 1985, 107, 4440; B. D. Martin, S. A. Matchett, J. R. Norton and O. P. Anderson, J. Am. Chem. Soc., 1985, 107, 7952; D. M. Roddick and J. E. Bercaw, Chem. Ber., 1989, 122, 1579; P. Hofmann, P. Stauffert, M. Frede and K. Tatsumi, Chem. Ber., 1989, 122, 1559; P. Hofmann, P. Stauffert, K. Tatsumi, A. Nakamura and R. Hoffmann, Organometallics, 1985, 4, 404; K. Tatsumi, A. Nakamura, P. Hofmann, R. Hoffmann, K. G. Moloy and T. J. Marks, J. Am. Chem. Soc., 1986, 108, 4467.
54. R. L. Miller, P. T. Wolczanski and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 10 422 and references cited therein; M. H. Chisholm, C. E. Hammond, V. J. Johnston, W. E. Streib and J. C. Huffman, J. Am. Chem. Soc., 1992, 114, 7056; B. C. Bates, Angew. Chem., Int. Ed. Engl., 1993, 32, 228.
55. R. L. Miller, P. T. Wolczanski and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 10 422 and references cited therein; M. H. Chisholm, C. E. Hammond, V. J. Johnston, W. E. Streib and J. C. Huffman, J. Am. Chem. Soc., 1992, 114, 7056; B. C. Bates, Angew. Chem., Int. Ed. Engl., 1993, 32, 228.
56. R. L. Miller, P. T. Wolczanski and A. L. Rheingold, J. Am. Chem. Soc., 1993, 115, 10 422 and references cited therein; M. H. Chisholm, C. E. Hammond, V. J. Johnston, W. E. Streib and J. C. Huffman, J. Am. Chem. Soc., 1992, 114, 7056; B. C. Bates, Angew. Chem., Int. Ed. Engl., 1993, 32, 228.
57. R. L. Jones and C. W. Rees, J. Chem. Soc. C, 1969, 2249, 2255 and references cited therein; F. W. Fowler, Angew. Chem., Int. Ed. Engl., 1971, 10, 135.
58. R. L. Jones and C. W. Rees, J. Chem. Soc. C, 1969, 2249, 2255 and references cited therein; F. W. Fowler, Angew. Chem., Int. Ed. Engl., 1971, 10, 135.
59. J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Activation, VCH, New York, 1990; Activation and Functionalization of Alkanes, ed. C. L. Hill, Wiley, New York, 1989; A. E. Shilov, Activation of Saturated Hydrocarbons by Transition Metal Complexes, Reidel, Ingham, MA, 1984; W. D. Jones and F. J. Feher, Acc. Chem. Res., 1989, 2, 91; A. D. Ryabov, Chem. Rev., 1990, 90, 403; A. Sen, Acc. Chem. Res., 1988, 21, 421; R. H. Crabtree, Chem. Rev., 1985, 85, 245.
60. J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Activation, VCH, New York, 1990; Activation and Functionalization of Alkanes, ed. C. L. Hill, Wiley, New York, 1989; A. E. Shilov, Activation of Saturated Hydrocarbons by Transition Metal Complexes, Reidel, Ingham, MA, 1984; W. D. Jones and F. J. Feher, Acc. Chem. Res., 1989, 2, 91; A. D. Ryabov, Chem. Rev., 1990, 90, 403; A. Sen, Acc. Chem. Res., 1988, 21, 421; R. H. Crabtree, Chem. Rev., 1985, 85, 245.
61. J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Activation, VCH, New York, 1990; Activation and Functionalization of Alkanes, ed. C. L. Hill, Wiley, New York, 1989; A. E. Shilov, Activation of Saturated Hydrocarbons by Transition Metal Complexes, Reidel, Ingham, MA, 1984; W. D. Jones and F. J. Feher, Acc. Chem. Res., 1989, 2, 91; A. D. Ryabov, Chem. Rev., 1990, 90, 403; A. Sen, Acc. Chem. Res., 1988, 21, 421; R. H. Crabtree, Chem. Rev., 1985, 85, 245.
62. J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Activation, VCH, New York, 1990; Activation and Functionalization of Alkanes, ed. C. L. Hill, Wiley, New York, 1989; A. E. Shilov, Activation of Saturated Hydrocarbons by Transition Metal Complexes, Reidel, Ingham, MA, 1984; W. D. Jones and F. J. Feher, Acc. Chem. Res., 1989, 2, 91; A. D. Ryabov, Chem. Rev., 1990, 90, 403; A. Sen, Acc. Chem. Res., 1988, 21, 421; R. H. Crabtree, Chem. Rev., 1985, 85, 245.
63. J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Activation, VCH, New York, 1990; Activation and Functionalization of Alkanes, ed. C. L. Hill, Wiley, New York, 1989; A. E. Shilov, Activation of Saturated Hydrocarbons by Transition Metal Complexes, Reidel, Ingham, MA, 1984; W. D. Jones and F. J. Feher, Acc. Chem. Res., 1989, 2, 91; A. D. Ryabov, Chem. Rev., 1990, 90, 403; A. Sen, Acc. Chem. Res., 1988, 21, 421; R. H. Crabtree, Chem. Rev., 1985, 85, 245.
64. J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Activation, VCH, New York, 1990; Activation and Functionalization of Alkanes, ed. C. L. Hill, Wiley, New York, 1989; A. E. Shilov, Activation of Saturated Hydrocarbons by Transition Metal Complexes, Reidel, Ingham, MA, 1984; W. D. Jones and F. J. Feher, Acc. Chem. Res., 1989, 2, 91; A. D. Ryabov, Chem. Rev., 1990, 90, 403; A. Sen, Acc. Chem. Res., 1988, 21, 421; R. H. Crabtree, Chem. Rev., 1985, 85, 245.
65. J. A. Davies, P. L. Watson, J. F. Liebman and A. Greenberg, Selective Hydrocarbon Activation, VCH, New York, 1990; Activation and Functionalization of Alkanes, ed. C. L. Hill, Wiley, New York, 1989; A. E. Shilov, Activation of Saturated Hydrocarbons by Transition Metal Complexes, Reidel, Ingham, MA, 1984; W. D. Jones and F. J. Feher, Acc. Chem. Res., 1989, 2, 91; A. D. Ryabov, Chem. Rev., 1990, 90, 403; A. Sen, Acc. Chem. Res., 1988, 21, 421; R. H. Crabtree, Chem. Rev., 1985, 85, 245.