Use of alkane elimination in the one-step synthesis of organoscandium complexes containing a new multidentate cyclopentadienyl ligand

Organometallics

Volumn 15, Issue 12, 1996, Pages 2720-2726

  Mu, Ying ^a   Piers, Warren E ^d   MacQuarrie, Donald C ^b   Zaworotko, Michael J ^b   Young Jr , Victor G ^c  

^a UNIVERSITY OF GUELPH   (Canada)

^b SAINT MARY S UNIVERSITY   (Canada)

^c University of Minnesota ^*  (United States)

^d UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000430237     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9600856     Document Type: Article

References (47)

1. (a) du Plooy, K. E.; Moll, U.; Wocadlo, S.; Massa, W.; Okuda, J. Organometallics 1995, 14, 3129 and references therein.
2. (b) Christoffers, J.; Bergman, R. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2266.
3. Jutzi, P.; Dahinaus, J. Coord. Chem. Rev. 1994, 137, 179.
4. Okuda, J. Comments Inorg. Chem. 1994, 16, 185.
5. (a) Shapiro, P. J.; Bunel, E.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1990, 9, 867.
6. (b) Shapiro, P. J.; Cotter, W. D.; Schaefer, W. P.; Labinger, J. A. Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4623.
7. (c) Piers, W. E.; Shapiro, P. J.; Bunel, E.; Bercaw, J. E. Synlett 1990, 1, 74.
8. (a) Stevens, J. C.; Timmers, F. J.; Wilson, D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S. Y. European Patent Application EP-416-815-A2, March 13, 1991 (Dow).
9. (b) Canich, J. A. PCT Application WO 91/04257, April 4, 1991 (Exxon).
10. (c) Canich, J. A. U.S. Patent 5,026,798, 1991 (Exxon).
11. (a) Hughes, A. K.; Meetsma, A.; Teuoen, J. H. Organometallics 1993, 12, 1936.
12. (b) Piers, W. E.; Mu, Y.; MacGillivray, L. R.; Zaworotko, M. J. Polyhedron 1995, 14, 1.
13. (a) Cotton, F. A.; Marks, T. J. Inorg. Chem. 1970, 9, 2802.
14. (b) Bonny, A.; Holmes-Smith, R. D.; Hunter, G.; Stobart, S. R. J. Am. Chem. Soc. 1982, 104, 1855.
15. (c) McMaster, A. D.; Stobart, S. R. J. Am. Chem. Soc. 1982, 104, 2109.
16. 13b
17. Abel, E. W.; Dunster, M. O. J. Organomet. Chem. 1971, 33, 161.
18. Flores, J. C.; Chien J. C. W.; Rausch, M. D. Organometallics 1994, 13, 4140.
19. Alkane elimination procedures for Cp ligand attachment are not unprecedented: (a) Deacon, G. B.; Newham, R. H. Aust. J. Chem. 1985, 38, 1757. (b) Booij, M. Kiers, N. H.; Heeres, H. J.; Teuben, J. H. J. Organomet. Chem. 1989, 364, 79. (c) Deacon, G. B.; Forsyth, C. M.; Patalinghug, W. C.; White, A. H.; Deitrich, A.; Schumann, H. Aust. J. Chem. 1992, 45, 567. (d) Nickias, P. N.; Devore, D. D.; Wilson, D. R. PCT Application, WO 93/08199, 1993 (Dow).
20. Alkane elimination procedures for Cp ligand attachment are not unprecedented: (a) Deacon, G. B.; Newham, R. H. Aust. J. Chem. 1985, 38, 1757. (b) Booij, M. Kiers, N. H.; Heeres, H. J.; Teuben, J. H. J. Organomet. Chem. 1989, 364, 79. (c) Deacon, G. B.; Forsyth, C. M.; Patalinghug, W. C.; White, A. H.; Deitrich, A.; Schumann, H. Aust. J. Chem. 1992, 45, 567. (d) Nickias, P. N.; Devore, D. D.; Wilson, D. R. PCT Application, WO 93/08199, 1993 (Dow).
21. Alkane elimination procedures for Cp ligand attachment are not unprecedented: (a) Deacon, G. B.; Newham, R. H. Aust. J. Chem. 1985, 38, 1757. (b) Booij, M. Kiers, N. H.; Heeres, H. J.; Teuben, J. H. J. Organomet. Chem. 1989, 364, 79. (c) Deacon, G. B.; Forsyth, C. M.; Patalinghug, W. C.; White, A. H.; Deitrich, A.; Schumann, H. Aust. J. Chem. 1992, 45, 567. (d) Nickias, P. N.; Devore, D. D.; Wilson, D. R. PCT Application, WO 93/08199, 1993 (Dow).
22. Alkane elimination procedures for Cp ligand attachment are not unprecedented: (a) Deacon, G. B.; Newham, R. H. Aust. J. Chem. 1985, 38, 1757. (b) Booij, M. Kiers, N. H.; Heeres, H. J.; Teuben, J. H. J. Organomet. Chem. 1989, 364, 79. (c) Deacon, G. B.; Forsyth, C. M.; Patalinghug, W. C.; White, A. H.; Deitrich, A.; Schumann, H. Aust. J. Chem. 1992, 45, 567. (d) Nickias, P. N.; Devore, D. D.; Wilson, D. R. PCT Application, WO 93/08199, 1993 (Dow).
23. (a) Mu, Y.; Piers, W. E.; MacDonald, M.-A.; Zaworotko, M. J. Can. J. Chem. 1995, 73, 2233.
24. (b) Lee, L.; Berg, D. J.; Bushnell, G. W. Inorg. Chem. 1994, 33, 5302.
25. 8,13b complexes of 1,2-substituted ligand can be isolated and characterized when ligand attachment reactions are carried out at -78 °C.
26. (b) Mu, Y.; Piers, W. E. Unpublished results.
27. R and S symbols were designated according to Cahn-Ingold-Prelog rules as outlined in: (a) Schlögel, K. Top. Stereochem. 1967, 1, 39. (b) Sloan, T. E. Top. Stereochem. (c) Stanley, K.; Baird, M. C. J. Am. Chem. Soc. 1975, 97, 6598.
28. R and S symbols were designated according to Cahn-Ingold-Prelog rules as outlined in: (a) Schlögel, K. Top. Stereochem. 1967, 1, 39. (b) Sloan, T. E. Top. Stereochem. (c) Stanley, K.; Baird, M. C. J. Am. Chem. Soc. 1975, 97, 6598.
29. R and S symbols were designated according to Cahn-Ingold-Prelog rules as outlined in: (a) Schlögel, K. Top. Stereochem. 1967, 1, 39. (b) Sloan, T. E. Top. Stereochem. (c) Stanley, K.; Baird, M. C. J. Am. Chem. Soc. 1975, 97, 6598.
30. Since there are four chiral centers in these dimers, 16 stereoisomers are possible, some of which are meso compounds. Half of them may be eliminated since the pseudocoordination site occupied by the bridging hydride ligands in each scandium coordination sphere can only lie beneath the two adjacent ring protons. The remaining stereoisomers are the three diastereomeric pairs of enantiomers and the meso compound shown in Chart 2.
31. 2 plane, and therefore, 3c is also a credible candidate for 3′.
32. Hortmann, K.; Brintzinger, H. H. New J. Chem. 1992, 16, 51.
33. Shannon, R. D. Acta Crystallogr. 1976, A32, 751.
34. For 8-coordinate scandium centers, the calculated values for Sc-N bond lengths would be 2.33 Å. The coordination number for compounds 3a and 4a can be considered to be 7 if one views the cyclopentadienyl donor as being three coordinate.
35. Bradley, D. C.; Chudzynska, H.; Hammond, M. E.; Hursthouse, M. B.; Motevalli, M.; Ruowen, W. Polyhedron 1992, 11, 375.
36. Shapiro, P. J.; Henling, L. M.; Marsh, R. E.; Bercaw, J. E. Inorg. Chem. 1990, 29, 4560.
37. 2) dative bonds are slightly shorter than this value, (a) McRitchie, D. D.; Palenik, R. C.; Palenik, G. J. Inorg. Chim. Acta 1976, 20, L27. (b) Arif, A. M.; Hart, F. A.; Hursthouse, M. B.; Thornton-Pett, M.; Zhu, W. J. Chem. Soc., Dalton Trans. 1984, 2449.
38. 2) dative bonds are slightly shorter than this value, (a) McRitchie, D. D.; Palenik, R. C.; Palenik, G. J. Inorg. Chim. Acta 1976, 20, L27. (b) Arif, A. M.; Hart, F. A.; Hursthouse, M. B.; Thornton-Pett, M.; Zhu, W. J. Chem. Soc., Dalton Trans. 1984, 2449.
39. 3·xTHF. Due to the larger size of yttrium, THF adducts were formed. Removal of THF via heating under vacuum was to a degree successful; however, at least two metalation reactions were also facile under these conditions leading to a complex mixture of products. This ligand thus appears less suited for preparing stable alkyl derivatives of yttrium.
40. Piers, W. E.; Blackwell, J.; Zaworotko, M. J. Unpublished results.
41. Arnold, J.; Hoffman, C. G.; Dawson, D. Y.; Hollander, F. J. Organometallics 1993, 12, 3645.
42. Hagadorn, J. R.; Arnold, J. Organometallics 1996, 15.
43. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.
44. Lappert, M. F.; Pearce, R. J. Chem. Soc., Chem. Commun. 1973, 126.
45. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. 4.
46. Gabe, E. J.; Le Page, Y.; Charland, J.-P.; Lee, F. L.; White, P. S. J. Appl. Crystallogr. 1989, 22, 384.
47. SHELXTL-Plus V5.0, Siemens Industrial Automation, Inc., Madison, WI.