Synthesis, stability, and complexation behavior of isolable salen-type N2S2 and N2SO ligands based on thiol and oxime functionalities

Inorganic Chemistry

Volumn 47, Issue 3, 2008, Pages 875-885

  Akine, Shigehisa ^a   Akimoto, Ayako ^a   Shiga, Takuya ^a   Oshio, Hiroki ^a   Nabeshima, Tatsuya ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 39749091148     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic701525c     Document Type: Article

References (80)

1. (a) Pfeiffer, P.; Breith, E.; Lübbe, E.; Tsumaki, T Liebigs Ann. Chem. 1933, 503, 84-130.
2. (b) Pfeiffer, P.; Hesse, T.; Pfitzner, H.; Scholl, W.; Thielert, H. J. Prakt. Chem. 1937, 149, 217-296.
3. (a) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
4. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214.
5. Rigamonti, L.; Demartin, F.; Forni, A.; Righetto, S.; Pasini, A. Inorg. Chem. 2006, 45, 10976-10989.
6. (a) Mockler, G. M.; Chaffey, G. W.; Sinn, E.; Wong, H. Inorg. Chem. 1972, 11, 1308-1314.
7. (b) Chjo, K.-H.; Jeong, B.-G.; Kim, J.-H.; Jeon, S.; Rim, C.-P.; Choi, Y.-K. Bull. Korean Chem. Soc. 1997, 18, 850-856.
8. (c) Kasumov, V. T.; Köksal, F. Spectrochim. Acta 2005, A61, 225-231.
9. (a) Narang, K. K.; Lal, R. A. Curr. Sci. 1977, 46, 401-403.
10. (b) Yampol'skaya, M. A.; Shova, S. G.; Gerbeleu, N. V.; Simonov, Y. A.; Bel'skii, V. K.; Dvorkin, A. A. Russ. J. Inorg. Chem. 1983, 28, 984-989.
11. (c) Palanchuk, S. V.; Lipkovskii, Y.; Arion, V. B.; Simonov, Y. A.; Gerbeleu, N. V. Russ. J. Coord. Chem. 1995, 21, 884-887.
12. (d) Ardakani, M. M.; Sadeghi, A.; Salavati-Niasari, M. Talanta 2005, 66, 837-843.
13. (a) Akine, S.; Taniguchi, T.; Nabeshima, T. Chem. Lett. 2001, 682-683.
14. (b) Akine, S.; Taniguchi, T.; Dong, W.; Masubuchi, S.; Nabeshima, T. J. Org. Chem. 2005, 70, 1704-1711.
15. (a) Akine, S.; Taniguchi, T.; Nabeshima, T. Angew. Chem., Int. Ed. 2002, 41, 4670-4673.
16. (b) Akine, S.; Taniguchi, T.; Saiki, T.; Nabeshima, T. J. Am. Chem. Soc. 2005, 127, 540-541.
17. (c) Akine, S.; Matsumoto, T.; Taniguchi, T.; Nabeshima, T. Inorg. Chem. 2005, 44, 3270-3274.
18. (d) Akine, S.; Taniguchi, T.; Nabeshima, T. Tetrahedron Lett. 2006, 47, 8419-8422.
19. (e) Akine, S.; Taniguchi, T.; Nabeshima, T. J. Am. Chem. Soc. 2006, 128, 15765-15774.
20. (f) Akine, S.; Taniguchi, T.; Matsumoto, T.; Nabeshima, T. Chem. Commun. 2006, 4961-4963.
21. (g) Akine, S.; Kagiyama, S.; Nabeshima, T. Inorg. Chem. 2007, 46, 9525-9527.
22. For related salamo-metal complexes, see: (a) Akine, S.; Taniguchi, T.; Nabeshima, T. Inorg. Chem. 2004, 43, 6142-6144.
23. (b) Akine, S.; Taniguchi, T.; Nabeshima, T. Chem. Lett. 2006, 35, 604-605.
24. (c) Akine, S.; Dong, W.; Nabeshima, T. Inorg. Chem. 2006, 45, 4677-4684.
25. (d) Akine, S.; Sunaga, S.; Taniguchi, T.; Miyazaki, H.; Nabeshima, T. Inorg. Chem. 2007, 46, 2959-2961.
26. (a) Corrigan, M. F.; West, B. O. Aust. J. Chem. 1976, 29, 1413-1427.
27. (b) Marini, P. J.; Murray, K. S.; West, B. O. J. Chem. Soc., Dalton Trans. 1983, 143-151.
28. (a) Hoyer, E.; Lorenz, B. Z. Chem. 1968, 8, 28-29.
29. (b) Bertini, I.; Sacconi, L.; Speroni, G. P. Inorg. Chem. 1972, 11, 1323-1326.
30. (c) Engeseth, H. R.; McMillin, D. R.; Ulrich, E. L. Inorg. Chim. Acta 1982, 67, 145-149.
31. (d) Dutton, J. C.; Fallon, G. D.; Murray, K. S. Inorg. Chem. 1988, 27, 34-38.
32. (a) Marini, P. J.; Murray, K. S.; West, B. O. J. Chem. Soc., Chem. Commun. 1981, 726-728.
33. (b) Marini, P. J.; Berry, K. J.; Murray, K. S.; West, B. O.; Irving, M.; Clark, P. E. J. Chem. Soc., Dalton Trans. 1983, 879-884.
34. Fallon, G. D.; Gatehouse, B. M.; Marini, P. J.; Murray, K. S.; West, B. O. J. Chem. Soc., Dalton Trans. 1984, 2733-2739.
35. (a) Yamamura, T.; Tadokoro, M.; Kuroda, R. Chem. Lett. 1989, 1245-1246.
36. (b) Yamamura, T.; Tadokoro, M.; Tanaka, K.; Kuroda, R. Bull. Chem. Soc. Jpn. 1993, 66, 1984-1990.
37. (c) Henderson, R. K.; Bouwman, E.; Reedijk, J.; Powell, A. K. Acta Crystallogr. 1996, C52, 2696-2698.
38. (d) Smeets, W. J. J.; Spek, A. L.; Henderson, R. K.; Bouwman, E.; Reedijk, J. Acta Crystallogr. 1997, C53, 1564-1566.
39. (a) Goswami, N.; Eichhorn, D. M. Inorg. Chem. 1999, 38, 4329-4333.
40. (b) Goswami, N.; Eichhorn, D. M. Inorg. Chim. Acta 2000, 303, 271-276.
41. (a) Fallon, G. D.; Gatehouse, B. M. Acta Crystallogr. 1976, B32, 97-101.
42. (b) Gomes, L.; Pereira, E.; de Castro, B. Acta Crystallogr. 1999, C55, 1061-1063.
43. (a) Corrigan, M. F.; Rae, I. D.; West, B. O. Aust. J. Chem. 1978, 31, 587-594.
44. (b) Toste, F. D.; Lough, A. J.; Still, I. W. J. Tetrahedron Lett. 1995, 36, 6619-6622.
45. (a) The Bioinorganic Chemistry of Nickel; Lancaster, J. R., Jr., Ed.; VCH Publishers: New York, 1988.
46. (b) Halcrow, M. A.; Christou, G. Chem. Rev. 1994, 94, 2421-2481.
47. (c) Doukov, T. I.; Iverson, T. M.; Seravalli, J.; Ragsdale, S. W.; Drennan, C. L. Science 2002, 298, 567-572.
48. (d) Wuerges, J.; Lee, J.-W.; Yim, Y.-I.; Yim, H.-S.; Kang, S.-O.; Carugo, K. D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 8569-8574.
49. Golden, M. L.; Rampersad, M. V.; Reibenspies, J. H.; Darensbourg, M. Y. Chem. Commun. 2003, 1824-1825.
50. (a) Nagata, K. Chem. Pharm. Bull. 1969, 17, 661-668.
51. (b) Vasil'chenko, I. S.; Mistryukov, A. E.; Kochin, S. G.; Sergienko, V. S.; Porai-Koshits, M. A.; Garnovskii, A. D. Russ. J. Inorg. Chem. 1992, 37, 527-529.
52. 1)], see: Akine, S.; Nabeshima, T. Inorg. Chem. 2005, 44, 1205-1207.
53. Dixon, D. W.; Weiss, R. H. J. Org. Chem. 1984, 49, 4487-4494.
54. Rahman, L. K. A.; Scrowston, R. M. J. Chem. Soc., Perkin Trans. 1 1983, 2973-2977.
55. (a) Rynbrandt, R. H.; Balgoyen, D. P. J. Org. Chem. 1978, 43, 1824-1825.
56. (b) Creed, T.; Leardini, R.; McNab, H.; Nanni, D.; Nicolson, I. S.; Reed, D. J. Chem. Soc., Perkin Trans. 1 2001, 1079-1085.
57. Beurskens, P. T.; Beurskens, G.; de Gelder, R.; Garcia-Granda, S.; Gould, R. O.; Israel, R.; Smits, J. M. M. The DIRDIF-99 program system; Crystallography Laboratory, University of Nijmegen: Nijmegen, The Netherlands, 1999.
58. Sheldrick, G. M. SHELXL 97, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
59. Pascal, P. Ann. Chim. Phys. 1910, 19, 5-70.
60. Gallagher, T.; Pardoe, D. A.; Porter, R. A. Tetrahedron Lett. 2000, 41, 5415-5418.
61. Gomes, L.; Pereira, E.; de Castro, B. J. Chem. Soc., Dalton Trans. 2000, 1373-1379.
62. (a) Clarke, K.; Hughes, C. G.; Scrowston, R. M. J. Chem. Soc., Perkin Trans. 1 1973, 356-359.
63. (b) Meth-Cohn, O.; Tarnowski, B. Synthesis 1978, 58-60.
64. (c) Lawson, A. J. J. Chem. Soc., Chem. Commun. 1981, 1238-1239.
65. (d) Lawson, A. J. Phosphorus Sulfur 1982, 12, 357-367.
66. (e) Rahman, L. K. A.; Scrowston, R. M. J. Chem. Soc., Perkin Trans. 1 1984, 385-390.
67. (a) Kersting, B. Eur. J. Inorg. Chem. 1999, 2157-2166.
68. (b) Brooker, S.; Caygill, G. B.; Croucher, P. D.; Davidson, T. C.; Clive, D. L. J.; Magnuson, S. R.; Cramer, S. P.; Ralston, C. Y. J. Chem. Soc., Dalton Trans. 2000, 3113-3121.
69. (c) Goswami, N.; Van Stipdonk, M. J.; Eichhorn, D. M. Inorg. Chem. Commun. 2003, 6, 86-89.
70. Frydendahl, H.; Toftlund, H.; Becher, J.; Dutton, J. C.; Murray, K. S.; Taylor, L. F.; Anderson, O. P.; Tiekink, E. R. T. Inorg. Chem. 1995, 34, 4467-4476.
71. (a) Boskovic, C.; Rusanov, E.; Stoeckli-Evans, H.; Güdel, H. U. Inorg. Chem. Commun. 2002, 5, 881-886.
72. (b) Nihei, M.; Hoshino, N.; Ito, T.; Oshio, H. Polyhedron 2003, 22, 2359-2362.
73. (c) Sieber, A.; Boskovic, C.; Bircher, R.; Waldmann, O.; Ochsenbein, S. T.; Chaboussant, G.; Güdel, H. U.; Kirchner, N.; van Slageren, J.; Wernsdorfer, W.; Neels, A.; Stoeckli-Evans, H.; Janssen, S.; Juranyi, F.; Mutka, H. Inorg. Chem. 2005, 44, 4315-4325.
74. Clemente-Juan, J. M.; Chansou, B.; Donnadieu, B.; Tuchagues, J.-P. Inorg. Chem. 2000, 39, 5515-5519.
75. The relatively smaller g value is presumably due to contamination of the diamagnetic impurity.
76. Fierro, C. M.; Murphy, B. P.; Smith, P. D.; Coles, S. J.; Hursthouse, M. B. Inorg. Chim. Acta 2006, 359, 2321-2327.
77. For examples, see: (a) Kato, M.; Muto, Y.; Jonassen, H. B.; Imai, K.; Harano, A. Bull. Chem. Soc. Jpn. 1968, 41, 1864-1870.
78. (b) Miners, J. O.; Sinn, E. Bull. Chem. Soc. Jpn. 1973, 46, 1457-1461.
79. (c) Nassiff, P. J.; Boyko, E. R.; Thompson, L. D. Bull. Chem. Soc. Jpn. 1974, 47, 2321-2322.
80. Lewis, D. L.; Hatfield, W. E.; Hodgson, D. J. Inorg. Chem. 1972, 11, 2216-2221.