Determination of the Degree of Aggregation of Organocopper Compounds by Cryoscopy in Tetrahydrofuran

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 7, 1997, Pages 755-757

  Gerold, Andreas ^a   Jastrzebski, Johann T B H ^b   Kronenburg, Claudia M P ^b   Krause, Norbert ^a   Van Koten, Gerard ^b  

^a UNIVERSITY OF BONN   (Germany)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Aggregation; Copper; Cryoscopy; Lithium

Indexed keywords

EID: 0030818860     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199707551     Document Type: Article

References (60)

1. a) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959;
2. a) Y. Yamamoto, Angew. Chem. 1986, 98, 945-957; Angew. Chem. Int. Ed. Engl. 1986, 25, 947-959;
3. b) B. H. Lipshutz, Synthesis 1987, 325-341;
4. c) B. H. Lipshutz, Synlett 1990, 119-128;
5. d) B. H. Lipshutz, S. Sengupta, Org. React. 1992, 41, 135-631;
6. e) Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford. 1994;
7. f) B. H. Lipshutz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp, 283-382;
8. g) N. Krause, Metallorganische Chemie, Spektrum Akademischer Verlag, Heidelberg, 1996, pp. 175-200;
9. h) N. Krause, A. Gerold, Angew. Chem. 1997, 109, 194-213; Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
10. h) N. Krause, A. Gerold, Angew. Chem. 1997, 109, 194-213; Angew. Chem. Int. Ed. Engl. 1997, 36, 186-204.
11. a) C. Ullenius, B. Christenson, Pure Appl. Chem, 1988, 60, 57-64;
12. b) B. Chris- tenson, T. Olsson, C. Ullenius, Tetrahedron 1989, 45, 523-534;
13. c) S. H. Bertz, R. A. J. Smith, J. Am. Chem. Soc. 1989, 111, 8276-8277;
14. d) S. Sharma, A. C. Oehlschlager, Tetrahedron 1991, 47, 1177-1184;
15. e) N. Krause. J. Org. Chem. 1992, 57, 3509-3512;
16. f) N. Krause, R. Wagner, A. Gerold, J. Am. Chem. Soc. 1994, 116, 381-382;
17. g) A. S. Vellekoop, R. A. J., Smith, ibid. 1994, 116, 2902-2913;
18. h) E. S. M. Persson, M. van Klaveren, D. M. Grove, J. E. Bäckvall, G. van Koten, Chem. Eur. J. 1995, 1, 351-359 ;
19. i) K. Nilsson, C. Ullenius, N. Krause, J. Am. Chem. Soc. 1996, 118, 4194-4195.
20. Reviews: a) G. van Koten, J. Organomet, Chem. 1990, 400, 283-301; b) P. P. Power, Prog. Inorg. Chem. 1991, 39, 75-112; G. van Koten, S. L. James, J. T. B. H. Jastrzebski, in Comprehensive Organometallic Chemistry II Vol. 3 (Eds.: E. W Abel, F. G. A. Stone, G. Wilkinson), Pergamon/Elsevier, Oxford, 1995, pp. 57-133.
21. Reviews: a) G. van Koten, J. Organomet, Chem. 1990, 400, 283-301; b) P. P. Power, Prog. Inorg. Chem. 1991, 39, 75-112; G. van Koten, S. L. James, J. T. B. H. Jastrzebski, in Comprehensive Organometallic Chemistry II Vol. 3 (Eds.: E. W Abel, F. G. A. Stone, G. Wilkinson), Pergamon/Elsevier, Oxford, 1995, pp. 57-133.
22. Reviews: a) G. van Koten, J. Organomet, Chem. 1990, 400, 283-301; b) P. P. Power, Prog. Inorg. Chem. 1991, 39, 75-112; G. van Koten, S. L. James, J. T. B. H. Jastrzebski, in Comprehensive Organometallic Chemistry II Vol. 3 (Eds.: E. W Abel, F. G. A. Stone, G. Wilkinson), Pergamon/Elsevier, Oxford, 1995, pp. 57-133.
23. a) B. H. Lipshutz, J. A. Kozlowski, R. S. Wilhelm, J. Org. Chem. 1984, 49, 3943-3949;
24. b) B. H. Lipshutz, J. A. Kozlowski, C. M. Breneman, J. Am. Chem. Soc. 1985, 107, 3197-3204;
25. c) B. H. Lipshutz, J. A. Kozlowski, C. M. Brene- man, Tetrahedron Lett. 1985, 26, 5911-5914;
26. d) S. H. Bertz, G. Dabbagh, J. Am. Chem. Soc. 1988, 110, 3668-3670;
27. e)G, van Koten, J. T. B. H. Jastrzebski, Tetrahedron 1989, 45, 569-578;
28. f) S. H. Bertz, G. Dabbagh, X. He. P. P. Power. J. Am. Chem. Soc. 1993, 115, 11640-11641;
29. g) S. Sharma, A. C. Oehlschlager. J. Org. Chem. 1991, 56, 770-776;
30. h) R. D. Singer, A. C. Oehlschlager, ibid. 1991, 56, 3510-3514.
31. a) R. G. Pearson, C. D. Gregory, J. Am. Chem. Soc. 1976, 95, 4098-4104;
32. b) E. C. Ashby, J. J. Watkins, ibid. 1977, 99, 5312-5317.
33. a) S. H. Bertz, J. Am. Chem. Soc. 1990, 112, 4031-4032;
34. b) B. H. Lipshutz, S. Sharma, E. L. Ellsworth, ibid. 1990, 112, 4032-4034;
35. c) S. H. Bertz. ibid. 1991, 113, 5470-5471;
36. d) R. D. Singer, A. C. Oehlschlager, J. Org. Chem. 1992, 57, 2192-2195;
37. e) B. H. Lipshutz, B. James, ibid. 1994, 59, 7585-7587.
38. a) T. Stemmler, J. E. Penner-Hahn, P. Knochel, J. Am. Chem. Soc. 1993. 115, 348-350;
39. b) T. M. Barnhari, H. Huang, J. E. Penner-Hahn, J. Org. Chem. 1995, 60, 4310-4311;
40. T. L. Stemmler, T. M. Barnhart, J. E. Penner-Hahn, C. E. Tucker, P. Knochel, M. Böhme, G. Frenking, J. Am. Chem. Soc. 1995, 117, 12489-12497.
41. a) J. P. Snyder, D. P. Spangler, J. R. Behling, B. E. Rossiter, J. Org. Chem. 1994, 59, 2665-2667;
42. b) J. P. Snyder, S. H. Bertz, ibid. 1995. 60, 4312-4313;
43. c) S. H. Bertz, G. Miao, M. Eriksson, Chem. Commun. 1996, 815-816.
44. a) W. Bauer, D. Seebach, Helv. Chim. Acta 1984, 67, 1972-1988;
45. b) W. Bauer, W. R. Winchester, v. R. Schleyer, Organometallics 1987, 6., 2371-2379;
46. c) W. Zarges, M. Marsch, K. Harms, K Haller, G. Frenking, G. Boche, Chem. Ber. 1991, 124. 861-866;
47. d) H. Ahlbrecht, J. Harbach, T. Hauck, H. Kalinowski, ibid. 1992, 125, 1753-1762.
48. nom: nominal concentration of RLi; Z: number of molecules RLi bound per formula unit).
49. a) N. Krause, S. Arndt. Chem. Ber. 1993, 126, 261-263;
50. b) B. H. Lipshutz. K Kayser, K. Siegmann, Tetrahedron Lett. 1993, 34, 6693-6696;
51. c) B. H. Lip- shutz, K. Siegmann, E. Garcia, K. Kayser, J. Am. Chem. Soc. 1993, 115, 9276-9282.
52. 2]: δ = 159.9.
53. 2] supports the idea that a dynamic process is indeed operating. In contrast, sharp signals are detected for the corresponding "lower order" cupraies [RCu(CN)Li]. For a further discussion of the spectroscopic properties of cyanocuprateu, see H. Huang, K. Alvarez, Q. Lui, T. M. Barnhart, J. P. Snyder, J. E. Penner-Hahn, J. Am. Chem. Soc. 1996, 118, 8808-8816.
54. a) B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771-806;
55. b) N. Krause, Kontakte (Darmstadt) 1993 (1), 3-13.
56. a) A. Haubrich, M. van Klaveren, G. van Koten, G. Handke, N. Krause, J. Org. Chem. 1993, 55, 5849-5852;
57. b) G. van Koten, Pure Appl. Chem. 1994, 66, 1455-1462.
58. a) M. D. Janssen, PhD Thesis, Utrecht University, 1996;
59. b) M. D. Janssen. M. A. Corsten, A. L. Spek, D. M. Grove, G. van Koten, Organometallics 1996, 15, 2810-2820.
60. The dependence of the cryoscopic constants on the thermometer may be attributed to different heat conductabilities and immersion depths of the sensors used.