Synthesis and reactivity of [(DMSC)Ti(η2-OCAr2)L2] complexes (DMSC = dimethylsilyl-bridged p-tert-butylcalix[4]arene dianion, Ar = Aryl group, and L2 = delocalized diimine)

Organometallics

Volumn 22, Issue 1, 2003, Pages 136-144

  KIngston, Jesudoss V ^a   Sarveswaran, Vallipuram ^a,b   Parkin, Sean ^a   Ladipo, Folami T ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

^b UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CHARGE TRANSFER; COORDINATION REACTIONS; DISSOLUTION; KETONES; MICROANALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTIONS; SYNTHESIS (CHEMICAL); TITANIUM; X RAY CRYSTALLOGRAPHY;

ALKOXIDE GROUP; METAL TO DIIMINE LIGAND CHARGE TRANSFER; PHOTOCHEMICALLY ASSISTED TRANSFORMATION; TITANAPINACOLATE COMPLEXES;

ORGANOMETALLICS;

EID: 0037421481     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020487f     Document Type: Article

References (87)

1. (a) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6426.
2. (b) Armbruster, J.; Grabowski, S.; Ruch, T.; Prinzbach, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2242.
3. (c) Balu, N.; Banerji, A. J. Org. Chem. 1998, 63, 3468.
4. (d) Ojima, I.; Tzamarioudaki, M.; Zhaoyang, L.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
5. (e) Hill, J. E.; Balaich, G.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1993, 12, 2911.
6. (f) Kahn, B. E.; Rieke, R. D. Chem. Rev. 1988, 88, 733.
7. (g) Pons, J.-M.; Santelli, M. Tetrahedron 1988, 44, 4295.
8. (h) Schore, N. E. Chem. Rev. 1988, 88, 1081.
9. (i) Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Permagon: Oxford, 1991; Vol. 5, pp. 1163-1184.
10. (j) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1978, 109, 6551.
11. (a) Villiers, C.; Ephritikhine, M. Chem. Eur. J. 2001, 7, 3043.
12. (b) Eisch, J. J.; Gitua, J. N.; Otieno, P. O.; Shi, X. J. Organomet. Chem. 2001, 624, 229.
13. (c) Ephritikhine, M. J. Chem. Soc., Chem. Commun. 1998, 2549.
14. (d) Wirth, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 61.
15. (e) Furstner, A.; Bogdanovic, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2443.
16. (f) McMurry, J. E. Chem. Rev. 1989, 89, 1513.
17. (g) Dushin, R. G. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, 1996; Vol. 12, p 1071.
18. (a) Ozerov, O. V.; Parkin, S.; Brock, C. P.; Ladipo, F. T. Organometallics 2000, 19, 4187.
19. (b) Kingston, J. V.; Ozerov, O. V.; Parkin, S.; Brock, C. P.; Ladipo, F. T. J. Am. Chem. Soc. 2002 in press.
20. (a) Durfee, L. D.; Fanwick, P. E.; Rothwell, I. P.; Folting, K.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 4720.
21. (b) Corbin, D. R.; Willis, E. N.; Duesler, E. N.; Stucky, G. D. J. Am. Chem. Soc. 1980, 102, 5971.
22. (c) McPherson, A. M.; Fieselmann, B. F.; Lichtenberger, D. L.; McPherson, G. L.; Stucky, G. D. J. Am. Chem. Soc. 1979, 101, 3425.
23. See for example the following and references therein: (a) Helberg, L. E.; Gunnoe, T. B.; Brooks, B. C.; Sabat, M.; Harman, W. D. Organometallics 1999, 18, 573.
24. (b) Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Schreiber, S. L., Eds.; Pergamon: New York, 1991; Vol. 1, Chapter 1.10.
25. 1-ketone complexes, see: (a) Foxman, B. M.; Klemarczyk, P. T.; Liptrot, R. E.; Rosenblum, M. J. Organomet. Chem. 1980, 187, 253.
26. (b) Boudjouk, P.; Woell, J. B.; Radonovich, L. J.; Eyring, M. W. Organometallics 1982, 1, 582.
27. (c) Gambarotta, S.; Pasquali, M.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. Inorg. Chem. 1981, 20, 1173.
28. (d) Crabtree, R. H.; Hlatky, G. G.; Parnell, C. P.; Segmuller, B. E.; Uriarte, R. J. Inorg. Chem. 1984, 23, 354.
29. (e) Dalton, D. M.; Gladysz, J. A. J. Chem. Soc., Dalton Trans. 1991, 2741.
30. (f) Sunkel, K.; Urban, G.; Beck, W. J. Organomet. Chem. 1985, 290, 231.
31. (g) Cicero, R. L.; Protasiewicz, J. D. Organometallics 1995, 14, 4792.
32. (h) Bachand, B.; Wuest, J. D. Organometallics 1991, 10, 2015.
33. (i) Fachinetti, G.; Del Nero, S.; Floriani, C. J. Chem. Soc., Dalton Trans. 1976, 1046.
34. 2-ketones with alkyl or aryl substituents, see: (a) Williams, D. S.; Schofield, M. H.; Anhaus, J. T.; Schrock, R. R. J. Am. Chem. Soc. 1990, 112, 6728.
35. (b) Barry, J. T.; Chacon, S. T.; Chisholm, M. H.; Huffmann, J. C.; Streib, W. E. J. Am. Chem. Soc. 1995, 117, 1974.
36. (c) Harman, W. D.; Fairlie, D. P.; Taube, H. J. Am. Chem. Soc. 1986, 108, 8223.
37. (d) Hill, J. E.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1992, 11, 1771.
38. (e) Thorn, M. G.; Hill, J. E.; Warantuke, S. A.; Johnson, E. S.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630.
39. (f) Steinhuebel, D. P.; Lippard, S. J. J. Am. Chem. Soc. 1999, 121, 11762.
40. (g) Scott, M. J.; Lippard, S. J. J. Am. Chem. Soc. 1997, 119, 3411.
41. (h) Harman, W. D.; Sekine, M.; Taube, H. J. Am. Chem. Soc. 1988, 110, 2439.
42. (i) Okuda, J.; Herberich, G. E. Organometallics 1987, 6, 2331.
43. (a) Erker, G. Acc. Chem. Res. 1984, 17, 103.
44. (b) Kropp, K.; Skibbe, V.; Erker, G.; Kruger, C. J. Am. Chem. Soc. 1983, 105, 3353.
45. (c) Erker, G.; Hoffmann, U.; Zwetler, R.; Betz, P.; Kruger, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 630.
46. (d) Erker, G.; Czisch, P.; Schlund, R.; Angermund, K.; Kruger, C. Angew. Chem., Int. Ed. Engl. 1986, 25, 364.
47. (e) Stella, S.; Floriani, C. J. Chem. Soc., Chem. Commun. 1986, 1053.
48. (f) Erker, G.; Dorf, U.; Czisch, P.; Petersen, J. L. Organometallics 1986, 5, 668.
49. (g) Fachinetti, G.; Biran, C.; Floriani, C.; Villa, A. C.; Guastini, C. Inorg. Chem. 1978, 17, 2995.
50. 2O}] (2) with 1,10-phenanthroline (1 equiv) in pentane at low temperatures (-78 to 0 °C) was unsuccessful. No reaction was observed at -78 °C, and a mixture of products resulted as the reaction mixture was warmed.
51. 2)] (8) occurs.
52. (a) Ozerov, O. V.; Patrick, B. O.; Ladipo, F. T. J. Am. Chem. Soc. 2000, 122, 6423.
53. (b) Ozerov, O. V.; Ladipo, F. T.; Patrick, B. O. J. Am. Chem. Soc. 1999, 121, 7941.
54. (c) Fan, M.; Zhang, H.; Lattman, M. Organometallics 1996, 15, 5216.
55. 1H and C NMR.
56. 2] was noted by Schrock. Wood, C. D.; Shrock, R. R. J. Am. Chem. Soc. 1979, 101, 5421.
57. 2CHOH, Sommer, A.; Stamm, H.; Woderer, A. Chem. Ber. 1988, 121, 387.
58. (a) Loukova, G. V.; Strelets, V. V. Collect. Czech. Chem. Commun. 2001, 66, 185.
59. (b) Vleck, A. Jr. Coord. Chem. Rev. 1998, 177, 219.
60. (c) Flamini, A.; Giuliani, A. M. Inorg. Chim. Acta 1986, 112, L7.
61. (d) Fischer, E. O.; Aumann, R. J. Organomet. Chem. 1967, 9, P15.
62. (e) Calderazzo, F.; Salzmann, J. J.; Mosimann, P. Inorg. Chim. Acta 1967, 1, 65.
63. (a) Covert K. J.; Wolczanski, P. T. Inorg. Chem. 1989, 28, 4567.
64. (b) Covert, K. J.; Wolczanski, P. T.; Hill, S. A.; Krusic, P. J. Inorg. Chem. 1992, 31, 66.
65. Kingston, J. V.; Karapetyan, A.; Miller, A. F.; Ladipo, F. T. Unpublished results.
66. 2 = peak potential for further reduction of the radical anion.
67. b Krishnan, C. V.; Creutz, C.; Schwarz, H. A.; Sutin, N. J. Am. Chem. Soc. 1983, 105, 5617.
68. c Grimshaw, J.; Hamilton, R. J. Electroanal. Chem. 1980, 106, 339.
69. 1H NMR revealed 4 and 9 in ∼ 1: 2 ratio, along with minor amounts of unidentified DMSC-containing products.
70. 2-aldehydes has been attributed to both steric crowding and the higher energy of the π* orbital for ketones relative to the π* orbital for aldehydes.
71. Ozerov, O. V.; Brock, C. P.; Carr, S.; Parkin, S.; Ladipo, F. T. Organometallics 2000, 19, 5016.
72. 13C NMR chemical shift values for 8-11.
73. 2 group, see for example: Agapie, T.; Diaconescu, P. L.; Mindiola, D. J.; Cummins, C. C. Organometallics 2002, 21, 1329, and ref 16b.
74. 26
75. Kim, I.; Nishihara, Y.; Jordan, R. F.; Rogers, R. D.; Rheingold, A. L.; Yap, G. P. A. Organometallics 1997, 16, 3314.
76. Doherty, S.; Errington, R. J.; Jarvis, A. P.; Collins, S.; Clegg, W.; Elsegood, M. R. J. Organometallics 1998, 17, 3408.
77. Space group Cc was chosen in preference to C2/c for a number of reasons. No satisfactory structure solution could be obtained in C2/c. The two molecules per asymmetric unit in the Cc model could, however, be almost superimposed by rotation about an axis that was almost, but not exactly, parallel with the crystallographic b axis. Moreover, the superposition was far from perfect, resulting in many geometric clashes. The program PLATON was similarly unsuccessful in reducing the Cc model to a satisfactory model in C2/c. The solvent, which was partially disordered in the Cc model, would have been hopelessly disordered in C2/c. Furthermore, the data collection had to be performed at 150 K owing to a destructive phase transition on cooling to below 150 K. It is quite possible that the symmetry of the structure is indeed C2/c at room temperature, but owing to the unstable nature of both the crystals and the molecule itself and the general weakness of the diffraction pattern, data collection at room temperature was not feasible.
78. Weak diffraction data were obtained due to the mediocre quality of the crystal utilized in the X-ray diffraction study. However, light atom positions in standards X-ray structure determinations are limited to about 0.02 Å, even for perfect data. See for example: (a) Coppens, P.; Sabine, T. M.; Delaplane, G.; Ibers, J. A. Acta Crystallogr. 1986, B42, 515.
79. (b) Allen, F. H. Acta Crystallogr. 1986, B42, 515.
80. In light of the similarity of the two molecules in the asymmetric unit, bond lengths and angles are given as the average over both molecules.
81. 4).
82. 2·)].
83. A nucleophilic aromatic substitution step is involved in the generally accepted mechanism for the Chichibabin reaction, through which heterocyclic nitrogen compounds can be aminated with alkali metal amides. See for example: (a) Smith, M. B.; March, J. March's Advanced Organic Chemistry; 2001; p 873.
84. (b) Vobruggen, H. Adv. Heterocycl. Chem. 1990, 49, 117.
85. (a) Wu, F.; Thummel, R. P. Inorg. Chim. Acta 2002, 327, 26.
86. (b) Kaizu, Y.; Yazaki, T.; Torii, Y.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1970, 43, 2068.
87. 2}phen] (6) in methylene chloride, strong bands are observed below 400 nm. In the visible region, the absorbance maximum for 5 and 6 are observed at 427 and 467 nm, respectively. The bathochromic shift of the absorbance maximum of 6 reflects the lower energy of the π* state of the 1,10-phenanthroline ligand.