Aluminum complexes incorporating bulky nitrogen and sulfur donor ligands

Organometallics

Volumn 17, Issue 18, 1998, Pages 4042-4048

  Coles, Martyn P ^a   Swenson, Dale C ^a   Jordan, Richard F ^a   Young Jr , Victor G ^b  

^a E11 SSH   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001308406     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9802358     Document Type: Article

References (113)

1. + species: Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1997, 119, 8125.
2. + species: Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1997, 119, 8125.
3. + species: Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1997, 119, 8125.
4. + species: Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1997, 119, 8125.
5. Coles, M. P.; Swenson, D. C.; Jordan, R. F.; Young, V. G., Jr. Organometallics 1997, 16, 5183.
6. Aeilts, S. L.; Coles, M. P.; Swenson, D. C.; Jordan, R. F.; Young, V. G., Jr. Organometallics, in press.
7. Stetter, H.; Wulff, C. Chem. Ber. 1962, 95, 2302.
8. Ogawa, K.; Akazawa, M. Japanese Pat. Appl. JP 91-164070 910410.
9. Ogawa, K.; Akazawa, M. Japanese Pat. Appl. JP 91-208987 910517.
10. Ziegler, K.; Krupp, F.; Weyer, K.; Larbig, W. Liebigs Ann. Chem. 1960, 629, 251.
11. (a) Takeda, N.; Inoue, S. Bull. Chem. Soc. Jpn. 1986, 51, 3564.
12. (b) Aida, T.; Inoue, S. J. Am. Chem. Soc. 1983, 105, 1304.
13. (c) Kojima, F.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1986, 108, 391.
14. (a) Wakatsuki, K.; Takeda, Y.; Tanaka, T. Inorg. Nucl. Chem. Lett. 1974, 10, 383.
15. (b) Uhl, W.; Vester, A.; Hiller, W. J. Organomet. Chem. 1993, 443, 9.
16. (a) Hirabayashi, T.; Imaeda, H.; Sakai, S.; Ishii, Y. J. Organomet. Chem. 1969, 19, 299.
17. (b) Hirabayashi, T.; Sakakibara, T.; Ishiii, Y. J. Organomet. Chem. 1972, 35, 19.
18. (a) Uhl, W.; Schütz, U.; Hiller, W.; Heckel, M. Chem. Ber. 1994, 127, 1587.
19. (b) Uhl, W.; Schütz, U.; Pohl, S.; Saak, W. Z. Anorg. Allg. Chem. 1996, 622, 373.
20. Weidlein, J. J. Organomet. Chem. 1973, 49, 257.
21. 2: δ-0.29.
22. (a) Kai, Y.; Yasuoka, N.; Kasai, N.; Kakudo, M. Bull. Chem. Soc. Jpn. 1972, 45, 3403.
23. (b) Kai, Y.; Yasouka, N.; Kasai, N.; Kakudo, M.; Yasuda, H.; Tani, H. J. Chem. Soc., Chem. Commun. 1970, 1243.
24. van Vliet, M. R. P., van Koten, G., de Keijser, M. S.; Vrieze, K. Organometallics 1987, 6, 1652.
25. Maringgele, W. Z. Anorg. Allg. Chem. 1981, 473, 133.
26. (a) Kai, Y.; Yasuoka, N.; Kasai, N.; Kakudo, M. Yasuda, H.; Tani, H. J. Chem. Soc., Chem. Commun. 1968, 1332.
27. (b) Kai, Y.; Yasuoka, N.; Kasai, N.; Kakudo, M. Yasuda, H.; Tani, H. J. Chem. Soc., Chem. Commun. 1969, 575.
28. (c) Kai, Y.; Yasuoka, N.; Kasai, N.; Kakudo, M. J. Organomet. Chem. 1971, 32, 165.
29. (d) Kai, Y.; Yasuoka, N.; Kasai, N.; Kakudo, M. Bull. Chem. Soc. Jpn. 1972, 45, 3388.
30. (e) Kai, Y.; Yasuoka, N.; Kasai, N.; Kakudo, M. Bull. Chem. Soc. Jpn. 1972, 45, 3397.
31. (f) Yasuda, H.; Araki, T.; Tani, H. J. Organomet. Chem. 1973, 49, 333.
32. (g) Yasuda, H.; Araki, T.; Tani, H. J. Organomet. Chem. 1973, 49, 103.
33. Lechler, R.; Hausen, H.-D.; Weidlein, J. J. Organomet. Chem. 1989, 359, 1.
34. Kottmair-Maieron, D.; Lechler, R.; Weidlein, J. Z. Anorg. Allg. Chem. 1991, 593, 111.
35. March, J. Advanced Organic Chemistry, 3rd ed.; John Wiley: New York, 1985; p 19.
36. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
37. Sutton, L. E. Interatomic Distances and Configuration in Molecules and Ions, Special Publications No. 18; The Chemical Society: London, 1965.
38. 3-character at the donor nitrogen atom (sum of angles = 359.6°, R′ substituent in the plane of the metallacycle).
39. (a) Hausen, H.-D.; Gerstner, F.; Schwarz, W. J. Organomet. Chem. 1978, 145, 277.
40. (b) Zhou, Y.; Richeson, D. S. Inorg. Chem. 1996, 35, 2448.
41. (c) Zhou, Y.; Richeson, D. S. Inorg. Chem. 1996, 35, 1423.
42. Zhou, Y.; Richeson, D. S. Inorg. Chem. 1997, 36, 501.
43. Close H-H contacts: H(6B)-H(28A) = 2.3 Å; H(6C)-H(31A) = 2.3 Å; H(5C)-H(19A) = 2.3 Å; H(7B)-H(16A) = 2.4 Å. Sum of van der Waals radii = 2.4 Å.
44. Close H-H contacts: H(5C)-H(12B) = 2.2 Å; H(3C)-H(12B) = 1.8 Å; H(3C)-H(14A) = 2.0 Å; H(3A)-H(14A) = 2.2 Å; H(5B)-H(24A) = 2.2 Å; H(4B)-H(24A) = 1.9 Å; H(4A)-H(23B) = 2.1 Å.
45. (a) Breunig, H. J.; Müller, D. Angew. Chem., Int. Ed. Engl. 1982, 21, 439.
46. (b) Ashe, A. J., III; Ludwig, E. G., Jr.; Oleksyszyn, J. Organometallics 1983, 2, 1859.
47. (c) Mundt, V. O.; Becker, G.; Rössler, M.; Witthauer, C. Z. Anorg. Allg. Chem. 1983, 506, 42.
48. (d) Calderazzo, F.; Poli, R.; Pelizzi, G. J. Chem. Soc., Dalton Trans. 1984, 2365.
49. (e) Ashe, A. J., III. Adv. Organomet Chem. 1990, 30, 77.
50. (f) Calderazzo, F.; Juris, A.; Poll, R.; Ungari, F. Inorg. Chem. 1991, 30, 1274.
51. (g) Spence, R. E. v. H.; Hsu, D. P.; Buchwald, S. L. Organometallics 1992, 11, 3492.
52. (h) Breunig, H. J.; Ebert, K. H.; Schulz, R. E.; Wieber, M.; Sauer, I. Z. Naturforsch. 1995, 50b, 735.
53. (i) Ashe, A. J., III; Al-ahmad, S. Adv. Organomet. Chem. 1996, 39, 325, and references therein.
54. Ar = 2,4,6-tris(bis(trimethylsilyl)methyl)phenyl: (a) Tokitoh, N.; Arai, Y.; Okazaki, R.; Nagase, S. Science 1997, 277, 78. (b) Tokitoh, N.; Arai, Y.; Sasamori, T.; Okazaki, R.; Nagase, S.; Uekusa, H.; Ohashi, Y. J. Am. Chem. Soc. 1998, 120, 433.
55. Ar = 2,4,6-tris(bis(trimethylsilyl)methyl)phenyl: (a) Tokitoh, N.; Arai, Y.; Okazaki, R.; Nagase, S. Science 1997, 277, 78. (b) Tokitoh, N.; Arai, Y.; Sasamori, T.; Okazaki, R.; Nagase, S.; Uekusa, H.; Ohashi, Y. J. Am. Chem. Soc. 1998, 120, 433.
56. Hartmann, H.; Habenicht, G.; Reiss, W. Z. Anorg. Allg. Chem. 1962, 317, 54.
57. Zorn, H.; Schindlbauer, H.; Hammer, D. Monatsh. Chem. 1967, 98, 731.
58. Wieber, M.; Baudis, U. Z. Anorg. Allg. Chem. 1978, 439, 134.
59. (a) Kauffmann, T.; Steinseifer, F.; Klas, N. Chem. Ber. 1985, 118, 1039.
60. (b) Wieber, M.; Rudolph, K. Z. Naturforsch. 1988, 436, 739.
61. (a) Wieber, M.; Sauer, I. Z. Naturforsch. 1984, 39b, 887.
62. (b) Wieber, M.; Sauer, I. Z. Naturforsch. 1987, 42b, 695.
63. (c) Breunig, H. J.; Müller, D. Z. Naturforsch. 1986, 41b, 1129.
64. (a) Cullen, W. R.; Wu, A. W. J. Fluorine Chem. 1976, 8, 183.
65. (b) Humphries, R. E.; Al-Jabar, N. A. A.; Bowen, D.; Massey, A. G.; Deacon, G. B. J. Organomet. Chem. 1987, 319, 59.
66. (a) Kollegger, G. M.; Siegl, H.; Hassler, K.; Gruber, K. Organometallics 1996, 15, 4337.
67. (b) Hassler, K.; Seidl, S. J. Organomet. Chem. 1988, 347, 27.
68. Carmalt, C. J.; Cowley, A. H.; Decken, A.; Lawson, Y. G.; Norman, N. C. Organometallics 1996, 15, 887.
69. (a) Goel, R. G.; Prasad, H. S. J. Organomet. Chem. 1972, 36, 323.
70. (b) Beaumont, R. E.; Goel, R. G.; Prasad, H. S. Inorg. Chem. 1973, 12, 944.
71. (c) Rüther, R.; Huber, F.; Preut, H. J. Organomet. Chem. 1988, 342, 185.
72. (d) Matano, Y.; Azuma, N.; Suzuki, H. J. Chem. Soc., Perkin Trans. 1 1994, 1739.
73. (e) Hassan, A.; Breeze, S. R.; Courtenay, S.; Deslippe, C.; Wang, S. Organometallics 1996, 15, 5613.
74. (a) Ignatious, F.; Sein, A.; Delaviz, Y.; Cabasso, I.; Smid, J. Polymer 1992, 33, 1724.
75. (b) Smid, J.; Cabasso, I.; Chatterjee, G. In Polymeric Materials Encyclopedia Vol. 10; Salamone, J. C., Ed.; CRC Press: New York, 1996; pp 7345-7350, and references therein.
76. Suzuki, H.; Kurata, H.; Matano, Y. J. Chem. Soc., Chem. Commun. 1997, 2295.
77. Several procedures have so far been reported for the generation of dilithiobenzenes. See: (a) Gilman, H.; Langham, W.; Moore, F. W. J. Am. Chem. Soc. 1940, 62, 2327. (b) Fang, M.-O.; Watanabe, A.; Matsuda, M. J. Organomet. Chem. 1995, 489, 15. (c) Fossatelli, M.; den Besten, R.; Verkruijsse, H. D.; Brandsma, L. Recl. Trav. Chim. Pays-Bas 1994, 113, 527.
78. Several procedures have so far been reported for the generation of dilithiobenzenes. See: (a) Gilman, H.; Langham, W.; Moore, F. W. J. Am. Chem. Soc. 1940, 62, 2327. (b) Fang, M.-O.; Watanabe, A.; Matsuda, M. J. Organomet. Chem. 1995, 489, 15. (c) Fossatelli, M.; den Besten, R.; Verkruijsse, H. D.; Brandsma, L. Recl. Trav. Chim. Pays-Bas 1994, 113, 527.
79. Several procedures have so far been reported for the generation of dilithiobenzenes. See: (a) Gilman, H.; Langham, W.; Moore, F. W. J. Am. Chem. Soc. 1940, 62, 2327. (b) Fang, M.-O.; Watanabe, A.; Matsuda, M. J. Organomet. Chem. 1995, 489, 15. (c) Fossatelli, M.; den Besten, R.; Verkruijsse, H. D.; Brandsma, L. Recl. Trav. Chim. Pays-Bas 1994, 113, 527.
80. Koo, S.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389.
81. Challenger, F.; Allpress, C. F. J. Chem. Soc. 1915, 107, 16.
82. 2 induced the oligomeric coupling to form 3a and 4a
83. 2 induced the oligomeric coupling to form 3a and 4a
84. 2 induced the oligomeric coupling to form 3a and 4a
85. (a) Rieke, R. D. Acc. Chem. Res. 1977, 10, 301.
86. (b) Rieke, R. D.; Bales, S. E. J. Am. Chem. Soc. 1974, 96, 1775.
87. House, H. O.; Chu, C.-Y.; Wilkins, J. M.; Umen, M. J. J. Org. Chem. 1975, 40, 1460.
88. Matano, Y.; Miyamatsu, T.; Suzuki, H. Organometallics 1996, 15, 1951.
89. Challenger, F. J. Chem. Soc. 1916, 109, 250.
90. 23b
91. 23b
92. 23b
93. 23b
94. 23b
95. 5 (25) Ortho-lithiated arenes have successfully been used for the preparation of ortho-sulfonyl-substituted triarylbismuthanes; see ref 14 and (a) Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. (b) Suzuki, H.; Murafuji, T. J. Chem. Soc., Chem. Commun. 1992, 1143. (c) Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
96. 5 (25) Ortho-lithiated arenes have successfully been used for the preparation of ortho-sulfonyl-substituted triarylbismuthanes; see ref 14 and (a) Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. (b) Suzuki, H.; Murafuji, T. J. Chem. Soc., Chem. Commun. 1992, 1143. (c) Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
97. 5 (25) Ortho-lithiated arenes have successfully been used for the preparation of ortho-sulfonyl-substituted triarylbismuthanes; see ref 14 and (a) Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1992, 1593. (b) Suzuki, H.; Murafuji, T. J. Chem. Soc., Chem. Commun. 1992, 1143. (c) Suzuki, H.; Murafuji, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1993, 1169.
98. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306. Ortholithiation of benzenesulfonamide, see: Watanabe, H.; Schwarz, R. A.; Hauser, C. R.; Lewis, J.; Slocum, D. W. Can. J. Chem. 1969, 47, 1543.
99. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306. Ortholithiation of benzenesulfonamide, see: Watanabe, H.; Schwarz, R. A.; Hauser, C. R.; Lewis, J.; Slocum, D. W. Can. J. Chem. 1969, 47, 1543.
100. Tomalia, D. A.; Baker, H.; Dewald, J. R.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polym. J. 1985, 17, 117.
101. Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003.
102. For example, see: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H.-B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Hawker, C. J.; Fréchet, J. M. J. In New Methods in Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, Scotland, 1995; pp 290-330.
103. For example, see: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H.-B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Hawker, C. J.; Fréchet, J. M. J. In New Methods in Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, Scotland, 1995; pp 290-330.
104. For example, see: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H.-B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Hawker, C. J.; Fréchet, J. M. J. In New Methods in Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, Scotland, 1995; pp 290-330.
105. For example, see: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138. (b) Mekelburger, H.-B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571. (c) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413. (d) Hawker, C. J.; Fréchet, J. M. J. In New Methods in Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, Scotland, 1995; pp 290-330.
106. Ginzberg, A. Ber. Dtsch. Chem. Ges. 1903, 36, 2703.
107. Structure solution methods: Calbrese, J. C. PHASE-Patterson Heavy Atom Solution Extractor. Ph.D. Thesis, University of Wisconsin-Madison, 1972. Beurskens, P. T. DIRDIF: Direct Method for Difference Structures - An Automatic Procedure for Phase Extension and Refinement of Difference Structure Factors; Technical Report 1984/1, Crystallography Laboratory, Toernoiveld, 6525 Ed Nijmegen, The Netherlands.
108. Structure solution methods: Calbrese, J. C. PHASE-Patterson Heavy Atom Solution Extractor. Ph.D. Thesis, University of Wisconsin-Madison, 1972. Beurskens, P. T. DIRDIF: Direct Method for Difference Structures - An Automatic Procedure for Phase Extension and Refinement of Difference Structure Factors; Technical Report 1984/1, Crystallography Laboratory, Toernoiveld, 6525 Ed Nijmegen, The Netherlands.
109. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. 4, Table 2.2 A.
110. Ibers, J. A.; Hamilton, W. C. Acta Crystallogr. 1964, 17, 781.
111. Cromer, D. T. Reference 32, Table 2.3.1.
112. TEXSAN-TEXRAY Structure Analysis Package; Molecular Structure Corp., The Woodlands, TX, 1985.
113. Johnson, C. K. ORTEP-II; Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.