Monomeric Alkyl and Hydride Derivatives of Zinc Supported by Poly(pyrazolyl)hydroborato Ligation: Synthetic, Structural, and Reactivity Studies

Organometallics

Volumn 14, Issue 1, 1995, Pages 274-288

  Looney, Adrian ^a   Han, Runyu ^a   Gorrell, Ian B ^a   Cornebise, Mark ^a   Yoon, Keum ^a   Parkin, Gerard ^a   Rheingold, Arnold L ^b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0141452494     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00001a041     Document Type: Article

References (55)

1. Boersma, J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 2, pp 823–862. (b) Coates, G. E.; Green, M. L. H.; Wade, K. Organometallic Compounds. Volume I: The Main Group Elements, 3rd ed.; Methuen: London, 1967. (c) Elschenbroich, C.; Salzer, A. Organometallics: A Concise Introduction, 2nd ed.; VCH: New York, 1992.
2. Miginiac, L. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Vol. 3, Chapter 2. (b) Furukawa, J.; Kawabata, N. Adv. Organomet. Chem. 1974, 12, 83–134. (c) Erdik, E. Tetrahedron 1992, 48, 9577–9648.
3. Trofimenko, S.; Calabrese, J. C.; Thompson, J. S. Inorg. Chem. 1987, 26, 1507–1514.
4. The nomenclature adopted here for tris(pyrazolyl)hydroborato ligands is based on that described by Trofimenko. Thus, the tris(pyrazolyl)hydroborato ligands are represented by the abbrevation Tp, with the 3- and 5-alkyl substituents listed, respectively, as superscripts. Similarly, the bis(pyrazolyl)hydroborato ligands are represented by the abbrevation Bp. See: Trofimenko, S. Chem. Rev. 1993, 93, 943–980.
5. Han, R.; Looney, A.; Parkin, G. J. Am. Chem. Soc, 1989, 111, 7276–7278. (b) Han, R.; Parkin, G. J. Am. Chem. Soc. 1990, 112, 3662–3663. (c) Han, R.; Parkin, G. Organometallics 1991, 10, 1010–1020. (d) Han, R.; Parkin, G. J. Am. Chem. Soc. 1992, 114, 748–757.
6. Gorrell, I. B.; Looney, A.; Parkin, G. J. Chem. Soc., Chem. Commun. 1990, 220-222. (b) Gorrell, I. B.; Looney, A.; Parkin, G.; Rheingold, A. L. J. Am. Chem. Soc. 1990, 112, 4068–4069. (c) Han, R.; Gorrell, I. B.; Looney, A. G.; Parkin, G. J. Chem. Soc., Chem. Commun. 1991, 717–719.
7. Han, R.; Parkin, G. Inorg. Chem. 1993, 32, 4968–4970.
8. Gilman, H.; Jones, R. G. J. Am. Chem. Soc. 1946, 68, 517–520.
9. Han, R.; Parkin, G. J. Organomet. Chem. 1990, 393, C43-C46.
10. Alsfasser, R.; Powell, A. K.; Vahrenkamp, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 898–899. (b) Alsfasser, R.; Powell, A. K.; Trofimenko, S.; Vahrenkamp, H. Chem. Ber. 1993, 126, 685–694.
11. Looney, A.; Saleh, A.; Zhang, Y.; Parkin, G. Inorg. Chem. 1994, 33, 1158–1164.
12. Reger, D. L.; Mason, S. S. Organometallics 1993, 12, 2600–2603.
13. Yoon, K.; Parkin, G. J. Am. Chem. Soc. 1991, 113, 8414–8418.
14. Pauling, L. The Nature of The Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, NY, 1960; p 256.
15. Spek, A. L.; Jastrzebski, J. T. B. H.; van Koten, G. Acta Crystallogr. 1987, C43, 2006–2007.
16. Engelhardt, L. M.; Jacobsen, G. E.; Patalinghug, W. C.; Skelton, B. W.; Raston, C. L.; White, A. H. J. Chem. Soc., Dalton Trans. 1991, 2859–2868.
17. Hursthouse, M. B.; Motevalli, M.; O'Brien, P.; Walsh, J. R.; Jones, A. C. Organometallics 1991, 10, 3196–3200.
18. Dekker, J.; Boersma, J.; Fernholt, L.; Haaland, A.; Spek, A. L. Organometallics 1987, 6, 1202—1206.
19. Parkin, G. Acc. Chem. Res. 1992, 25, 455–460. (b) Parkin, G. Chem. Rev. 1993, 93, 887–911.
20. Pajerski, A. D.; BergStresser, G. L.; Parvez, M.; Richey, H. G., Jr. J. Am. Chem. Soc. 1988, 110, 4844–4845.
21. Hartmann, F.; Kläui, W.; Kremer-Aach, A.; Mootz, D.; Strerath, A.; Wunderlich, H. Z. Anorg. Allg. Chem. 1993, 619, 2071–2076.
22. Yoon, K.; Parkin, G. Inorg. Chem. 1992, 31, 1656–1662.
23. Tolman, W. B. Inorg. Chem. 1991, 30, 4877–4880.
24. 4Cl) has been structurally characterized by X-ray diffraction: Kitajima, N.; Fujisawa, K.; Mor-oka, Y. J. Am. Chem. Soc. 1990, 29, 357–358.
25. Han, R.; Parkin, G. J. Am. Chem. Soc. 1991, 113, 9707–9708.
26. Han, R.; Looney, A.; McNeill, K.; Parkin, G.; Rheingold, A. L.; Haggerty, B. S. J. Inorg. Biochem. 1993, 49, 105–121.
27. Looney, A.; Han, R.; McNeill, K.; Parkin, G. J. Am. Chem. Soc. 1993, 115, 4690–4697.
28. 2 to give the trimethylsiloxide derivative: Han, R.; Parkin, G. Polyhedron 1990, 9, 2655–2657.
29. Looney, A.; Cornebise, M.; Miller, D.; Parkin, G. Inorg. Chem. 1992, 31, 989–992.
30. Eichorn, D. M.; Armstrong, W. H. Inorg. Chem. 1990, 29, 3607–3612.
31. De Koning, A. J.; Boersma, J.; van der Kerk, G. J. M. J. Organomet. Chem. 1980, 186, 159–172.
32. De Koning, A. J.; Boersma, J.; van der Kerk, G. J. M. J. Organomet. Chem. 1980, 195, 1-12. (b) Ashby, E. C.; Goel, A. B. Inorg. Chem. 1981, 20, 1096–1101. (c) De Koning, A. J.; Boersma, J.; van der Kerk, G. J. M. Tetrahedron Lett. 1977, 2547–2548.
33. Bell, N. A.; Coates, G. E. J. Chem. Soc. A 1968, 823–826. (b) Bell, N. A.; Moseley, P. T.; Shearer, H. M. M.; Spencer, C. B. J. Chem. Soc., Chem. Commun. 1980, 359–360. (c) Bell, N. A.; Moseley, P. T.; Shearer, H. M. M.; Spencer, C. B. Acta Crystallogr. 1980, B36, 2950—2954.
34. Neils, T. L.; Burlitch, J. M. Inorg. Chem. 1989, 28, 1607-1609.
35. Goeden, G. V.; Caulton, K. G. J. Am. Chem. Soc. 1981, 103, 7354–7355.
36. De Koning, A. J.; Boersma, J.; van der Kerk, G. J. M. J. Organomet. Chem. 1978, 155, C5-C7.
37. Han, R.; Parkin, G. Inorg. Chem. 1992, 31, 983–988.
38. 2. (a) Bell, N. A.; Coates, G. E.; Schneider, M. L.; Shearer, H. M. M. J. Chem. Soc., Chem. Commun. 1983, 828–829. (b) Bell, N. A.; Coates, G. E.; Schneider, M. L.; Shearer, H. M. M. Acta Crystallogr. 1984, C40, 608–610.
39. Reger, D. L.; Mason, S. S.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 10406–10407. (b) Reger, D. L.; Mason, S. S.; Rheingold, A. L. J. Am. Chem. Soc. 1994, 116, 2233.
40. -1 invariably have unidentate coordination: Deacon, G. B.; Phillips, R. J. Coord. Chem. Rev. 1980, 33, 227–250.
41. Gruff, E. S.; Koch, S. A. J. Am. Chem. Soc. 1989, 111, 8762–8763. (b) Goel, S. C.; Chiang, M. Y.; Buhro, W. E. Inorg. Chem. 1990, 29, 4646–4652. (c) Bochmann, M.; Bwembya, G.; Grinter, R.; Lu, J.; Webb, K. J.; Williamson, D. J.; Hursthouse, M. B.; Mazid, M. Inorg. Chem. 1993, 32, 532–537. (d) Bochmann, M.; Bwembya, G. C.; Grinter, R.; Powell, A. K; Webb, K. J.; Hursthouse, M. B.; Malik, K. M. A.; Mazid, M. A. Inorg. Chem. 1994, 33, 2290–2296. (e) Goel, S. C.; Chiang, M. Y.; Buhro, W. E. J. Am. Chem. Soc. 1990, 112, 5636–5637. (f) Bonasia, P. J.; Arnold, J. Inorg. Chem. 1992, 31, 2508–2514. (g) Power, P. P.; Shoner, S. C. Angew. Chem., Int. Ed. Engl. 1990, 29, 1403–1404. (h) Arif, A. M.; Cowley, A. H.; Jones, R. A.; Koschmieder, S. U. J. Chem. Soc., Chem. Commun. 1987, 1319–1320. (i) Petersen, R. B.; Ragosta, J. M.; Whitwell, G. E., II; Burlitch, J. M. Inorg. Chem. 1983, 22, 3407–3415. (j) Romanenko, V. D.; Shul'gin, V. F.; Skopenko, V. V.; Markovskii, L. N. Zh. Obshchei Khim. 1984, 54, 2791-2792; J. General Chem. (Engl. Transl.) 1985, 2501–2502.
42. Chernega, A. N.; Antipin, M. Y.; Struchkov, Y. T.; Romanenko, V. D. Koord. Chim. 1989, 15, 894–901.
43. Purdy, A. P.; George, C. F. Organometallics 1992, 11, 1955–1959.
44. Westerhausen, M.; Rademacher, B.; Schwarz, W. Z. Anorg. Allg. Chem. 1993, 619, 675–689.
45. Olmstead, M. M.; Power, P. P.; Shoner, S. C. J. Am. Chem. Soc. 1991, 113, 3379–3385.
46. Parvez, M.; BergStresser, G. L.; Richey, H. G., Jr. Acta Crystallogr. 1992, C48, 641–644.
47. Bell, N. A.; Shearer, H. M. M.; Spencer, C. B. Acta Crystallogr. 1983, C39, 1182–1185. (b) Budzelaar, P. H. M.; Alberts-Jansen, H. J.; Mollema, K; Boersma, J.; van der Kerk, G. J. M.; Spek, A. L.; Duisenberg, A. J. M. J. Organomet. Chem. 1983, 243, 137–148. (c) Al-Juaid, S. S.; Buttrus, N. H.; Eaborn, C.; Hitchcock, P. B.; Roberts, A. T. L.; Smith, J. D. S.; Sullivan, A. C. J. Chem. Soc., Chem. Commun. 1986, 908–909.
48. 2 due to an intermolecular Zn-O interaction [2.252(4) Å]. The C-Zn-C bond angle is 152.3(3)°: Gais, H.-J.; Bülow, G.; Raabe, G. J. Am. Chem. Soc. 1993, 115, 7215–7218.
49. Alsfasser, R.; Trofimenko, S.; Looney, A.; Parkin, G.; Vahrenkamp, H. Inorg. Chem. 1991, 30, 4098—4100.
50. The reference value for a pure single covalent Zn—O bond has been adopted to be 1.89 A: Haaland, A. Angew. Chem., Int. Ed. Engl. 1989, 28, 992–1000.
51. Paolucci, G.; Cacchi, S.; Caglioti, L. J. Chem. Soc., Perkin Trans. 1 1979, 1129–1131.
52. McNally, J. P.; Leong, V. S.; Cooper, N. J. ACS Symp. Ser. 1987, No. 357, 6–23. (b) Burger, B. J.; Bercaw, J. E. ACS Symp. Ser. 1987, No. 357, 79–97.
53. George, P. D.; Sommer, L. H.; Whitmore, F. C. J. Am. Chem. Soc. 1953, 75, 1585–1588.
54. Trofimenko, S. J. Am. Chem. Soc. 1967, 89, 6288–6294.
55. Sheldrick, G. M. SHELXTL, An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data; University of Göttingen, Göttingen, Federal Republic of Germany, 1981.