New chiral amide ligands derived from (±)-irans-1,2-Diaminocyclohexane. Applications in titanium (IV) chemistry

Organometallics

Volumn 16, Issue 7, 1997, Pages 1392-1400

  Tsuie, Barbara ^a   Swenson, Dale C ^a   Jordan, Richard F ^a   Petersen, Jeffrey L ^b  

^a E11 SSH   (United States)

^b WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001661287     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960939m     Document Type: Article

References (51)

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13. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
14. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
15. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
16. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
17. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
18. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
19. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
20. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
21. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
22. 2 chemistry: (a) Andersen, R. A. Inorg. Chem. 1979, 18, 2928. (b) Andersen, R. A. J. Organomet. Chem. 1980, 192, 189. (c) Planalp, R. P.; Andersen, R. A.; Zalkin, A. Organometallics 1983, 2, 16. (d) Bürger, V. H.; Wiegl, K. Z. Anorg. Allg. Chem. 1973, 398, 257. (e) Bürger, V. H.; Neese, H. J. Z. Anorg. Allg. Chem. 1969, 370, 275. (f) Bürger, V. H.; Kluess, C.; Neese, H. J. Z. Anorg. Allg. Chem. 1971, 387, 198. (g) Minhas, R. K.; Scoles, L.; Wong, S.; Gambarotta, S. Organometallics 1996, 15, 1113. (h) Herrmann, W. A.; Huber, N. W.; Behm, J. Chem. Ber. 1992, 125, 1405. (i) Horton, A. D.; de With, J. J. Chem. Soc., Chem. Commun. 1996, 1375. (j) Canich, J. M.; Turner, H. W. World Patent 92/12162, 1992. (k) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273. (l) Shah, S. A. A.; Dorn, H.; Voigt, A.; Roesky, H. W.; Parisini, E.; Schmidt, H. G.; Noltemeyer, M. Organometallics 1996, 15, 3176.
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39. 4. Due to these symmetry properties, the NMR spectra of both isomers have the same number of resonances.
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41. 0 M-R bonds by halogens, see: (a) Labinger, J. A.; Hart, D. W.; Seibert, W. E.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 3851. (b) Ho, S. C. H.; Straus, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1984, 106, 1533. (c) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S. C. H.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733.
42. 0 M-R bonds by halogens, see: (a) Labinger, J. A.; Hart, D. W.; Seibert, W. E.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 3851. (b) Ho, S. C. H.; Straus, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 1984, 106, 1533. (c) Brown-Wensley, K. A.; Buchwald, S. L.; Cannizzo, L.; Clawson, L.; Ho, S. C. H.; Meinhardt, D.; Stille, J. R.; Straus, D.; Grubbs, R. H. Pure Appl. Chem. 1983, 55, 1733.
43. For leading references relating to characterization of metalbenzyl bonding, see refs 1a and 1c and: (a) Crowther, D. J.; Borkowsky, S. L.; Swenson, D.; Meyer, T. Y.; Jordan, R. F. Organometallics 1993, 12, 2897. (b) Hughes, A. K.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (c) Latesky, S. L.; McMullen, A. K.; Niccolai, G. P.; Rothwell, I. P.; Huffman, J. C. Organometallics 1985, 4, 902.
44. For leading references relating to characterization of metalbenzyl bonding, see refs 1a and 1c and: (a) Crowther, D. J.; Borkowsky, S. L.; Swenson, D.; Meyer, T. Y.; Jordan, R. F. Organometallics 1993, 12, 2897. (b) Hughes, A. K.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (c) Latesky, S. L.; McMullen, A. K.; Niccolai, G. P.; Rothwell, I. P.; Huffman, J. C. Organometallics 1985, 4, 902.
45. For leading references relating to characterization of metalbenzyl bonding, see refs 1a and 1c and: (a) Crowther, D. J.; Borkowsky, S. L.; Swenson, D.; Meyer, T. Y.; Jordan, R. F. Organometallics 1993, 12, 2897. (b) Hughes, A. K.; Meetsma, A.; Teuben, J. H. Organometallics 1993, 12, 1936. (c) Latesky, S. L.; McMullen, A. K.; Niccolai, G. P.; Rothwell, I. P.; Huffman, J. C. Organometallics 1985, 4, 902.
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48. Zucchini, U.; Albizzati, E.; Giannini, U. J. Organomet. Chem. 1871, 26, 357.
49. The thermal decomposition of 12a,b was not studied in detail. Possible decomposition pathways include metalation of the Si-Me groups to yield metallacyclic products and a-H abstraction to yield Ti methylene species. For related chemistry, see: (a) Simpson, S. J.; Andersen, R. A. Inorg. Chem. 1981, 20, 3627. (b) Scoles, L.; Minhas, R.; Duchateau, R.; Jubb, J.; Gambarotta, S. Organometallics 1994, 13, 4978.
50. The thermal decomposition of 12a,b was not studied in detail. Possible decomposition pathways include metalation of the Si-Me groups to yield metallacyclic products and a-H abstraction to yield Ti methylene species. For related chemistry, see: (a) Simpson, S. J.; Andersen, R. A. Inorg. Chem. 1981, 20, 3627. (b) Scoles, L.; Minhas, R.; Duchateau, R.; Jubb, J.; Gambarotta, S. Organometallics 1994, 13, 4978.
51. SHELXL-93 is a FORTRAN-77 program (Professor G. Sheldrick, Institut für Anorganische Chemie, University of Göttingen, D-37077 Göttingen, Germany) for single-crystal X-ray structural analyses.