Synthesis and properties of the titanaoxacyclobutane derived from (Me5C5)2Ti(O)(L) and allene

Organometallics

Volumn 15, Issue 5, 1996, Pages 1446-1450

  Schwartz, David J ^a   Smith III, Milton R ^a   Andersen, Richard A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000100025     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950634s     Document Type: Article

References (43)

1. (a) Jorgensen, K. A.; Schiott, B. Chem. Rev. 1990, 90, 1483.
2. (b) Sundermeyer, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1144.
3. (a) Ho, S. C.; Hentges, S.; Grubbs, R. A. Organometallics 1988, 7, 780.
4. (b) Bazan, G. C.; Schrock, R. R.; O'Regan, M. B. Organometallics 1991, 10, 1062.
5. (c) Whinnery, L. L.; Henling, L. M.; Bercaw, J. E. J. Am. Chem. Soc. 1991, 113, 7575.
6. (d) Herrmann, W. A.; Wang, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1641.
7. (e) Beckhaus, R.; Strauss, I.; Wagner, T.; Kiprof, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 264.
8. (f) Beckhaus, R.; Wagner, T.; Zimmermann, C.; Herdtweck, E. J. Organomet. Chem. 1993, 460, 181.
9. (a) Day, V. W.; Klemperer, W. G.; Lockledge, S. P.; Main, D. J. Am. Chem. Soc. 1990, 112, 2031.
10. (b) Day, V. W.; Eberspacher, T. A.; Klemperer, W. G.; Zhong, B. J. Am. Chem. Soc. 1994, 116, 3119.
11. (a) Vaughn, G. A.; Hillhouse, G. L.; Lum, R. T.; Buchwald, S. L.; Rheingold, A. L. J. Am. Chem. Soc. 1988, 110, 7215.
12. (b) Vaughn, G. A.; Sofield, C. D.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1989, 111, 5493.
13. (c) Vaughn, G. A.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1990, 112, 7994.
14. (d) Carney, M. J.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 8751.
15. (e) Carney, M. J.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1990, 112, 6426.
16. (f) Matsunaga, P. T.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 2075.
17. (a) Hamilton, J. G.; Mackey, O. N. D.; Rooney, J. J.; Gilheany, D. G. J. Chem. Soc., Chem. Commun. 1990, 1600.
18. (b) Leonarda, M.; Pahor, N. B.; Calligaris, M.; Graziani, M.; Randaccio, L. J. Chem. Soc., Dalton Trans. 1978, 279.
19. (c) Schlodder, R.; Ibers, J. A.; Lenarda, M.; Grazini, M. J. Am. Chem. Soc. 1974, 96, 6893.
20. (d) Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics. 1991, 10, 3344.
21. (e) Klein, D. P.; Hayes, J. C.; Bergman, R. G. J. Am. Chem. Soc. 1988, 110, 3704.
22. (f) Zlota, A. A.; Frolow, F.; Milstein, D. J. Am. Chem. Soc. 1990, 112, 6411.
23. Smith, M. R., III; Matsunaga, P. T.; Andersen, R. A. J. Am. Chem. Soc. 1993, 115, 7049.
24. Polse, J. L.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 5393.
25. 2TiXY compounds is 2.40 Å, and the average Ti-ring centroid distance is 2.09 Å.
26. Thewalt, U.; Wohrle, T. J. Organomet. Chem. 1994, 464, C17.
27. Moloy, K. G.; Marsella, J. A.; Caulton, K. G. J. Am. Chem. Soc. 1980, 102, 3009.
28. Shiott, B.; Jorgensen, K. A. J. Chem. Soc., Dalton Trans. 1993, 337.
29. Interatomic Distance, Suppl. 1; The Chemical Society: London, 1965.
30. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
31. Legon, A. C. Chem. Rev. 1980, 80, 231.
32. 5 derivatives. This low barrier is also consistent with the possibility that the puckering of the metallacycle ring of 2 in the solid state results from crystal packing effects.
33. 2]: Seyferth, D.; Wang, T.; Davis, W. M. Organometallics 1994, 13, 4134. We thank Professor Seyferth for a copy of this paper.
34. Proulx, G.; Bergman, R. G. J. Am. Chem. Soc. 1995, 117, 6382.
35. This is a qualitative statement only, as the extent of 2 → 3 conversion varies from sample to sample.
36. (a) Bercaw, J. E.; Brintzinger, H. H. J. Am. Chem. Soc. 1991, 93, 2045.
37. (b) Miller, F. D.; Sanner, R. D. Organometallics 1988, 7, 818.
38. 8-toluene, below ca. -30°C. The ratio of the two isomers is ca. 2:1. Most likely, the two isomers result from slowing of rotation about the Ti-O bond, at the lower temperatures.
39. Schwartz, D. J.; Andersen, R. A. J. Am. Chem. Soc. 1995, 117, 4014.
40. 1H NMR). Stirring the reaction solution for longer periods of time results in more difficulty in isolating pure samples of 2; this is likely a result of slight conversion of 2 to 3 during this longer reaction time.
41. All calculations were performed on a DEC Microvax II or a DEC Microvax 4000 using locally modified Nonius-SDP software operating under Micro-VMS operating system.
42. (a) Frenz, B. A. In Structure Determination Package Users Guide; Texas A & M University and Enraf-Nonius: College Station, TX, and Delft, The Netherlands, 1985.
43. (b) Fair, C. K. In MolEN Molecular Structure Solution Procedures; Enraf-Nonius, Delft Instruments, X-ray Diffraction BV: Delft, The Netherlands, 1990.