Aryl calcium compounds: Syntheses, structures, physical properties, and chemical behavior

Angewandte Chemie - International Edition

Volumn 46, Issue 12, 2007, Pages 1950-1956

  Westerhausen, Matthias ^a   Gärtner, Martin ^a   Fischer, Reinald ^a   Langer, Jens ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Calcium; Direct synthesis; Grignard reagents; Organocalcium chemistry; Synthetic methods

Indexed keywords

MICROSTRUCTURE; PHYSICAL PROPERTIES; REACTION KINETICS; SOLVENTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DIRECT SYNTHESIS; GRIGNARD REAGENTS; ORGANOCALCIUM CHEMISTRY; SYNTHETIC METHODS;

CALCIUM COMPOUNDS;

EID: 34250820510     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604192     Document Type: Short Survey

References (82)

1. D. Seyferth, Organometallics 2006, 25, 2-24.
2. a) W. N. Setzer, P. von R. Schleyer, Adv. Organomet. Chem. 1985, 24, 353-451;
3. b) C. Schade, P. von R. Schleyer, Adv. Organomet. Chem. 1987, 27, 169-278.
4. a) C. Elschenbroich, A. Salzer, Organometallics: A Concise Introduction, 2nd ed., Weinheim, VCH, 1992;
5. b) Grignard Reagents New Developments (Ed.: H. G. Richey), Wiley, Chichester, 2000.
6. B. G. Gowenlock, W. E. Lindsell, J. Organomet. Chem. Libr. 1977, 1-73.
7. J. J. Eisch, R. B. King, Organometallic Synthesis, Vol. 2, Academic Press, New York, 1981, p. 101.
8. R. Zerger, G. Stucky, J. Organomet. Chem. 1974, 80, 7-17.
9. a) P. Jutzi, Adv. Organomet. Chem. 1986, 26, 217-295;
10. b) P. Jutzi, J. Organomet. Chem. 1990, 400, 1-17;
11. c) T. P. Hanusa, Polyhedron 1990, 9, 1345-1362;
12. d) T. P. Hanusa, Chem. Rev. 1993, 93, 1023-1036;
13. e) D. J. Burkey, T. P. Hanusa, Comments Inorg. Chem. 1995, 17, 41-77;
14. f) P. Jutzi, N. Burford in Metallocenes (Eds.: A. Togni, R. L. Halterman), Wiley-VCH, Weinheim, 1998, chap. 1, pp. 3-54;
15. g) M. L. Hays, T. P. Hanusa, Adv. Organomet. Chem. 1996, 40, 117-170;
16. h) P. Jutzi, N. Burford, Chem. Rev. 1999, 99, 969-990;
17. i) T. P. Hanusa, Organometallics 2002, 21, 2559-2571.
18. a) T. P. Hanusa, Coord. Chem. Rev. 2000, 210, 329-367;
19. b) M. Westerhausen, Angew. Chem. 2001, 113, 3063-3065;
20. Angew. Chem. Int. Ed. 2001, 40, 2975-2977;
21. c) J. S. Alexander, K. Ruhlandt-Senge, Eur. J. Inorg. Chem. 2002, 2761-2774.
22. F. G. N. Cloke, P. B. Hitchcock, M. F. Lappert, G. A. Lawless, B. Royo, J. Chem. Soc. Chem. Commun. 1991, 724-726.
23. C. Eabom, S. A. Hawkes, P. B. Hitchcock, J. D. Smith, Chem. Commun. 1997, 1961-1962.
24. a) F. Feil, S. Harder, Organometallics 2000, 19, 5010-5015;
25. b) S. Harder, F. Feil, A. Weeber, Organometallics 2001, 20, 1044-1046;
26. c) S. Harder, F. Feil, Organometallics 2002, 21, 2268-2274;
27. d) F. Feil, C. Müller, S. Harder, J. Organomet. Chem. 2003, 683, 56-63;
28. e) S. Harder, S. Müller, E. Hübner, Organometallics 2004, 23, 178-183.
29. V. Knapp, G. Müller, Angew. Chem. 2001, 113, 187-190;
30. Angew. Chem. Int. Ed. 2001, 40, 183-186.
31. E. Beckmann, Ber. Dtsch. Chem. Ges. 1905, 38, 904-906.
32. P. R. Markies, T. Nomoto, G. Schat, O. S. Akkerman, F. Bickelhaupt, W. J. J. Smeets, A. L. Spek, Organometallics 1991, 10, 3826-3837.
33. a) K. Mochida, H. Ogawa, J. Organomet. Chem. 1983, 243, 131-135;
34. b) K. Mochida, Y. Hiraga, H. Takeuchi, H. Ogawa, Organometallics 1987, 6, 2293-2297;
35. c) J. P. Dunne, M. Tacke, C. Selinka, D. Stalke, Eur. J. Inorg. Chem. 2003, 1416-1425.
36. S. Harder, J. Brettar, Angew. Chem. 2006, 118, 3554-3558;
37. Angew. Chem. Int. Ed. 2006, 45, 3474-3478.
38. C. Ruspic, S. Harder, Organometallics 2005, 24, 5506-5508.
39. R. Fischer, H. Görls, M. Westerhausen, Inorg. Chem. Commun. 2005, 8, 1159-1161.
40. S.-O. Hauber, F. Lissner, G. B. Deacon, M. Niemeyer, Angew. Chem. 2005, 117, 6021-6025;
41. Angew. Chem. Int. Ed. 2005, 44, 5871-5875.
42. M. Westerhausen, Coord. Chem. Rev. 1998, 176, 157-210.
43. a) W. C. Johnson, M. F. Stubbs, A. E. Sidwell, A. Pechukas, J. Am. Chem. Soc. 1939, 61, 318-329;
44. b) W. J. McCreary, J. Met. 1958, 10, 615-617;
45. c) J. Evers, A. Weiss, E. Kaldis, J. Muheim, J. Less-Common Met. 1973, 30, 83-95.
46. S. R. Drake, D. J. Otway, J. Chem. Soc. Chem. Commun. 1991, 517-519; Erratum: S. R. Drake, D. J. Otway, J. Chem. Soc. Chem. Commun. 1991, 1060.
47. H. Bönnemann, B. Bogdanovic, R. Brinkmann, N. Egeler, R. Benn, I. Topalovic, K. Seevogel, Main Group Met. Chem. 1990, 13, 341-362.
48. a) R. D. Rieke, Science 1989, 246, 1260-1264;
49. b) T.-C. Wu, H. Xiong, R. D. Rieke, J. Org. Chem. 1990, 55, 5045-5051;
50. c) M. J. McCormick, K. B. Moon, S. R. Jones, T. P. Hanusa, J. Chem. Soc. Chem. Commun. 1990, 778-779.
51. K. J. Klabunde, Acc. Chem. Res. 1975, 8, 393-399.
52. D. C. Bradley, M. B. Hursthouse, A. A. Ibrahim, K. M. Abdul Malik, M. Motevalli, R. Möseler, H. Powell, J. D. Runnacles, A. C. Sullivan, Polyhedron 1990, 9, 2959-2964.
53. a) J. S. Alexander, K. Ruhlandt-Senge, Angew. Chem. 2001, 113, 2732-2734;
54. Angew. Chem. Int. Ed. 2001, 40, 2658-2660;
55. b) J. S. Alexander, K. Ruhlandt-Senge, H. Hope, Organometallics 2003, 22, 4933-4937.
56. R. Fischer, M. Gärtner, H. Görls, M. Westerhausen, Organometallics 2006, 25, 3496-3500.
57. R. Fischer, M. Gärtner, H. Görls, M. Westerhausen, Angew. Chem. 2006, 118, 624-627;
58. Angew. Chem. Int. Ed. 2006, 45, 609-612.
59. M. Gärtner, H. Görls, M. Westerhausen, Synthesis 2007, in press.
60. R. Fischer, M. Gärtner, H. Görls, L. Yu, M. Reiher, M. Westerhausen, Angew. Chem., DOI: 10.1002/ange.20064436;
61. Angew. Chem. Int. Ed., DOI: 10.1002/anie.20064436.
62. J. Langer, M. Westerhausen, unpublished results.
63. M. Gärtner, H. Görls, M. Westerhausen, Organometallics 2007, in press.
64. a) P. B. Hitchcock, M. F. Lappert, G. A. Lawless, B. Royo, J. Chem. Soc. Chem. Commun. 1990, 1141-1143;
65. b) K. F. Tesh, T. P. Hanusa, J. C. Huffman, C. J. Huffman, Inorg. Chem. 1992, 31, 5572-5579.
66. M. Westerhausen, M. Hartmann, N. Makropoulos, B. Wieneke, M. Wieneke, W. Schwarz, D. Stalke, Z. Naturforsch. B 1998, 53, 117-125.
67. M. Westerhausen, W. Schwarz, Z. Anorg. Allg. Chem. 1991, 604, 127-140.
68. M. Westerhausen, W. Schwarz, Z. Naturforsch. B 1992, 47, 453-459.
69. J. J. Ritter, R. D. Anderson, J. Org. Chem. 1959, 24, 208-210;
70. see also: F. W. Swamer, G. A. Reynolds, C. R. Hauser, J. Org. Chem. 1951, 16, 43-46.
71. M. Westerhausen, Dalton Trans. 2006, 4755-4768.
72. M. Westerhausen, C. Gückel, H. Piotrowski, M. Vogt, Z. Anorg. Allg. Chem. 2002, 628, 735-740.
73. R. Fischer, M. Westerhausen, unpublished results.
74. a) W. Biltz, G. F. Hüttig, Z. Anorg. Allg. Chem. 1920, 114, 241-265;
75. b) R. Juza, H. Schumacher, Z. Anorg. Allg. Chem. 1963, 324, 278-286;
76. c) R. Juza, Angew. Chem. 1964, 76, 290-300;
77. d) N. Mammano, M. J. Sienko, J. Solid State Chem. 1970, 1, 534-535.
78. G. Bruhat, V. Thomas, C. R. Hebd. Seances Acad. Sci. 1926, 183, 297-299.
79. M. Fossatelli, R. den Besten, H. D. Verkruijsse, L. Brandsma, Recl. Trav. Chim. Pays-Bas 1994, 113, 527-528.
80. K. B. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The Carbon Copy, Chichester, Wiley, 1998.
81. M. Westerhausen, M. H. Digeser, H. Nöth, T. Seifert, A. Pfitzner, J. Am. Chem. Soc. 1998, 120, 6722-6725.
82. M. Westerhausen, M. H. Digeser, H. Nöth, W. Ponikwar, T. Seifert, K. Polborn, Inorg. Chem. 1999, 38, 3207-3214.