Use of Manganese(II)-Schiff Base Complexes for Carrying Polar Organometallics and Inorganic Ion Pairs

Inorganic Chemistry

Volumn 36, Issue 10, 1997, Pages 2178-2186

  Gallo, Emma ^a   Solari, Euro ^a   Floriani, Carlo ^a   Chiesi Villa, Angiola ^b   Rizzoli, Corrado ^b  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001399186     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9614069     Document Type: Article

References (112)

1. (a) Henrick, K.; Tasker, P. A.; Lindoy, L. L. In Progress in Inorganic Chemistry; Lippard. S. J., Ed.; Wiley: New York, 1985; Vol 33, p 1.
2. (b) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
3. Guerriero, P.; Tamburini, S.; Vigato, P. A. Coord. Chem. Rev. 1995, 139, 17.
4. Habata, Y.; Akabori, S. Coord. Chem. Rev. 1996, 148, 97.
5. (e) Hiraoka, M. Crown Ethers and Analogous Compounds; Elsevier: New York, 1992; Vol. 45, p 485.
6. (f) Weber, E.; Toner, J. L.; Goldberg, I.; Vögtle, F.; Laidler, D. A.; Stoddart, J. F.; Bartsch, R. A.; Wotta, C. L. Crown Ethers and Analogs; Wiley: New York, 1989; p 588.
7. (g) Cooper, S. R. Crown Compounds Toward Future Applications; VCH: New York, 1992; p 325.
8. (h) Lehn, J.-M. Science 1985, 279, 1177.
9. Lah, M. S.; Pecoraro, V. L. Comments Inorg. Chem. 1990, 11, 59.
10. (j) Gibney, B. R.; Wang, H.; Kampf, J. W.; Pecoraro, V. L. Inorg. Chem. 1996, 35, 6184.
11. (k) Gutsche, C. D. Calixarenes: a Versatile Class of Macrocyclic Compounds; Kluwer. Boston, MA, 1991; Vol. 3.
12. (a) Fachinetti, G.; Floriani, C.; Zanazzi, P. F. J. Am. Chem. Soc. 1978, 100, 7405.
13. (b) Eady, R. R.; Smith, B. E. In Dinitrogen Fixation; Hardy, R. W. F., Ed.; Wiley: New York, 1978; Vol. 2, p 399.
14. Avdeef, A.; Schaefer, W. P. J. Am. Chem. Soc. 1976, 98, 5153.
15. Gall, R. S.; Schaefer, W. P. Inorg. Chem. 1976, 75, 2758.
16. (e) Gall, R. S.; Rogers, J. F.; Schaefer, W. P.; Christoph, G. G. J. Am. Chem. Soc. 1976, 98, 5135.
17. (f) Schaefer, W. P.; Huie, B. T.; Kuilla, M. G.; Ealich, S. Inorg. Chem. 1980, 79, 340.
18. (g) Crumbliss, A. L.; Basolo, F. Science 1969, 164, 1168.
19. (h) Crumbliss, A. L.; Basolo, F. J. Am. Chem. Soc. 1970, 92, 55.
20. Gibson, D. H.; Ye, M.; Richardson, J. F. J. Am. Chem. Soc. 1992, 114, 9716.
21. (j) Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747.
22. (a) Reetz, M. T. In Organotitanium Reagents in Organic Synthesis; Springer: Berlin, 1986.
23. (b) Reetz, M. T. In Organometallics in Synthesis: A Manual; Schlosser, M., Ed.; Wiley: New York, 1994; Chapter 3.
24. Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth. B. Chem. Ber. 1985. 118, 1441,
25. Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259.
26. (e) Morris, R. J.; Girolami, G. S. Organometallics 1991, 10, 792.
27. (f) Quan, R. W.; Bazan, G. C.; Kiely, A. F.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4489.
28. (g) De Angelis, S.; Solari, E.; Floriani C.; Chiesi Villa, A.; Rizzoli, C. Organometallics 1995, 14, 4505.
29. (a) Lipshutz, B. H.; Sengupta, S. In Organic Reactions: Paquette, L. A., Ed.; Wiley: New York, 1992; Vol. 41, Chapter 2.
30. (b) Lipshutz, B. H. In Organometallics in Synthesis: A Manual; Schlosser, M., Ed.; Wiley: New York, 1994; Chapter 4.
31. (a) Tamura, M.; Kochi, J. J. Organomet. Chem, 1971, 29, 111.
32. (b) Howard, C. G.; Wilkinson, G.; Thornton-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1983, 2025.
33. Howard, C. G.; Girolami, G. S.; Wilkinson, G.; Thormon-Pett, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1983, 2631.
34. Girolami, G. S.; Wilkinson, G.; Thornton-Pett, M.; Hursthouse, M. B. J. Am. Chem, Soc. 1983, 105. 6752.
35. (e) Bartlett, R. A.; Olmstead, M. M.; Power, P. P.; Shoner, S. C. Organometallics 1988, 7, 1807.
36. (a) Veya, P.; Cozzi, P. G.; Floriani, C.; Rotzinger, F. P.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1995, 14, 4101 and references therein. Brace, W.; Laube, T.; Seebach, D. Chem. Ber. 1985, 118, 764. Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373.
37. (a) Veya, P.; Cozzi, P. G.; Floriani, C.; Rotzinger, F. P.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1995, 14, 4101 and references therein. Brace, W.; Laube, T.; Seebach, D. Chem. Ber. 1985, 118, 764. Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373.
38. (a) Veya, P.; Cozzi, P. G.; Floriani, C.; Rotzinger, F. P.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1995, 14, 4101 and references therein. Brace, W.; Laube, T.; Seebach, D. Chem. Ber. 1985, 118, 764. Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1373.
39. (b) Cozzi, P. G.; Veya, P.; Floriani, C.; Rotzinger, F. P.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1995, 14, 4092 and references therein. Paterson, I.; Cardin, D. J.; Lappert, M. F.; Raston, C. L. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 2.
40. (b) Cozzi, P. G.; Veya, P.; Floriani, C.; Rotzinger, F. P.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1995, 14, 4092 and references therein. Paterson, I.; Cardin, D. J.; Lappert, M. F.; Raston, C. L. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 2.
41. Schinzer, D.; Bärmann, H. Angew. Chem., Int. Ed, Engl 1996, 35, 1678.
42. jacoby, D.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. J. Am. Chem. Soc. 1993, 115, 3595.
43. (a) Wieghardt, K. Angew. Chem., Int. Ed. Engl. 1989, 28, 1153.
44. (b) Pecoraro, V. L.; Baldwin, M. J.; Gelasco, A. Chem. Rev. 1994, 94, 807.
45. Manganese Redox Enzymes; Pecoraro, V. L., Ed.; VCH: New York, 1992.
46. (a) Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309.
47. (b) Menage, S.; Collomb-Dunand Sauthier, M. N.; Lambeaux, C.; Fontecave, M. J. Chem. Soc., Chem. Commun. 1994, 1885.
48. Eilmes, J. Polyhedron 1992, 11, 581.
49. O'Connor, K. J.; Wey, S. J.; Burrows, C. J. Tetrahedron Lett. 1992, 33, 1001.
50. (e) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
51. (f) Reddy, D. R.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172.
52. (a) Normant, J. F.; Cahiez, G. In Modern Synthetic Methods; Scheffold, R., Ed.; Wiley: Chichester, U.K., 1983; Vol. 3, p 173.
53. (b) Cahiez, G.; Alami, M. Tetrahedron 1989, 45, 4163.
54. Cahiez, G.; Marquais, S. Synlett 1993, 45.
55. Cahiez, G.; Figadere, B.; Clery, P. Tetrahedron Lett. 1994, 35, 3065.
56. (e) Cahiez, G.; Chau, K.; Clery, P. Tetrahedron Lett. 1994, 35, 3069.
57. (f) Corey, E. J.; Posner, G. H. Tetrahedron Lett. 1970, 315.
58. (g) Reetz, M. T.; Haning, H. Tetrahedron Lett. 1993, 34, 7395.
59. (h) Reetz, M. T.; Haning, H.; Stanchev, S. Tetrahedron Lett. 1992, 33, 6963.
60. Reetz, M. T.; Rolling, K.; Griebenow, N. Tetrahedron Lett. 1994, 35, 1969.
61. (a) Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296.
62. (b) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
63. Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 1939.
64. Brandes, B. D.; Jacobsen, E. N. J. Org. Chem, 1994, 59, 4378.
65. (e) Pospisil, P. J.; Garsten, D. H.; Jacobsen, E. N. Chem. Eur. J. 1996, 2, 974.
66. (a) Stemmler, A. J.; Kampf, J. W.; Kirk, M. L.; Pecoraro, V. L. J. Am. Chem. Soc. 1995, 117, 6368.
67. (b) Stemmler, A. J.; Kampf, J. W.; Pecoraro, V. L. Inorg. Chem. 1995, 34, 2271.
68. Galio, E.; Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometallics 1995, 14, 2156.
69. Soiari, E.; Musso, F.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Organometaliics 1995, 14, 2265.
70. O'Connor, C. J. Prog. Inorg. Chem. 1982, 29, 203.
71. Lawton, S. L.; Jacobson, R. A. TRACER, a cell reduction program, Ames Laboratory, Iowa State University of Science and Technology. 1965.
72. Lehmann, M. S.; Larsen, F. K. Acta Crystalhgr., Sect. A: Cryst. Phys. Diffr. Theor. Gen. Crystallogr, 1974, A30, 580.
73. Data reduction, structure solution, and refinement were carried out on an IBM PS2 personal computer and on an Encore 91 computer.
74. Wilson, A. J. C. Nature (London) 1942, 750, 151.
75. o absorption correction. Comput. Chem. 1987, 11, 109.
76. North, A. C. T.; Phillips, D. C.; Mathews, F. S. Acta Crystallogr., Sect. A: Cryst. Phys., Diffr., Theor. Gen. Crystallogr. 1968, A24, 351.
77. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV: (a) p 99; (b) p 149.
78. Stewart, R. F.; Davidson, E. R.; Simpson, W. T. J. Chem. Phys. 1965, 42, 3175
79. Sheldrick, G. M. SHELX-76, Program for crystal structure determination; University of Cambridge: Cambridge, England, 1976.
80. Sheldrick, G. M. SHELXL92, Program for crystal structure refinement; University of Göttingen: Göttingen, Germany, 1992.
81. See the paragraph at the end of the paper regarding the Supporting Information
82. (a) Calligaris, M.; Randaccio, L. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford, U.K., 1987.
83. (b) Calligaris, M.; Nardin, G.; Randaccio, L. Coord. Chem. Rev. 1972, 7, 385.
84. Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Casey, C. P., Eds.; Pergamon: Oxford, U.K., 1981; Vol. 6.
85. (a) Morris, R. J.; Girolami, G. S. Organometallics 1991, 10, 792.
86. (b) Moms, R. J.; Girolami, G. S. Organometallics 1991, 10, 799.
87. Andersen, R. A.; Carmona-Guzman, E.; Gibson, J. F.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 2204.
88. Koschmieder, S. U.; Wilkinson, G.; Hussain-Bates, B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1992, 19.
89. Rosset, J.-M; Fioriani, C.; Mazzanti, M.; Chiesi-Villa, A.; Guastini, C. Inorg. Chem. 1990, 29, 3991.
90. Latten, J. L.; Dickson, R. S.; Deacon, G. B.; West, B. O.; Tiekink, E. R. T. J. Organomet. Chem. 1992, 435, 101.
91. (a) Sweany, R. L. In Comprehensive Organometallic Chemistry II; Abel, E. W. Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 8, Chapter 1, p 42 and references therein,
92. (b) Pratt, J. M.; Craig, P. J. Adv. Organomet. Chem. 1973, 11, 404.
93. Bigotto, A.; Costa, G.; Mestroni, G.; Pellizzer, G.; Puxeddu, A.; Reisenhofer, E.; Stefani, L.; Tauzher, G. Inorg. Chim. Acta 1970, 4, 41.
94. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361 and references therein.
95. (e) Dodd, D.; Johnson, M. D. J. Organomet. Chem. 1973, 52, 1.
96. (f) Pratt, J. M; Craig, P. J. Adv. Organomet. Chem. 1973, 11, 414.
97. (g) Randaccio, L.; Bresciani-Pahor, N.; Zangrando, E.; Marzilli, L. G. Chem. Soc. Rev. 1989, 18, 225.
98. (h) Charlaud, J.-P.; Zangrando, E.; Bresciani-Pahor, N.; Randaccio, L.; Marzilli, L. G. Inorg. Chem. 1993. 32, 4256.
99. De Angelis, S.; Solari, E.; Gallo, E.; Floriani, C.; ChiesiVilla, A.; Rizzou, C. Inorg. Chem. 1996, 35, 5995 and references therein.
100. (a) Floriani, C.; Solari, E.; Corazza, F.; Chiesi-Villa, A.; Guastini, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 64.
101. (b) Solari, E.; Floriani, C.; Chiesi-Villa, A.; Rizzoii, C. J. Chem. Soc., Dalton Trans. 1992, 367.
102. Unpublished results.
103. Reetz, M. T.; Stanchev, S.; Haning, H. Tetrahedron 1992, 48, 6813.
104. (a) Posner, G. H. Org. React. 1972, 19. 1.
105. (b) Wollenberg R. H.; Alibizati, K. F.; Perles, R. J. Am. Chem. Soc. 1977, 99 7365
106. Corey, E. J.; Beames, D. J. J. Am. Chem. Soc. 1972, 94, 7210.
107. Bertz J. H.; Dabbagh, G. J. Org. Chem. 1984, 49, 1119.
108. (e) Bertz, J. H.; Dabbagh, G.; Villacorta, G. M. J. Am. Chem. Soc. 1982, 104, 5824.
109. Cahiez, G.; Alami, M. Tetrahedron Lett. 1989, 30, 7365.
110. Cahiez, G.; Alami, M. Tetrahedron Lett. 1989, 30, 3541.
111. Cahiez, G.; Alami, M. Tetrahedron Lett. 1986, 27, 569.
112. Due to the absence of any peculiar structural interest, this structure is not reported.