From a cyclobutadiene dianion to a cyclobutadiene: Synthesis and structural characterization of tetrasilyl-substituted cyclobutadiene

Angewandte Chemie - International Edition

Volumn 40, Issue 9, 2001, Pages 1675-1677

  Sekiguchi, Akira ^a   Tanaka, Masanobu ^a   Matsuo, Tsukasa ^a   Watanabe, Hidetoshi ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Carbanions; Cycloalkenes; Oxidation; Small ring systems; Solid state structures

Indexed keywords

DERIVATIVES; OXIDATION; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

DIANIONS;

ORGANIC COMPOUNDS;

1,3 BUTADIENE DERIVATIVE; ANION; CYCLOALKENE;

ARTICLE; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SOLID STATE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0035805270     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20010504)40:9<1675::AID-ANIE16750>3.0.CO;2-G     Document Type: Article

References (56)

1. For a review, see G. Maier, Angew. Chem. 1988, 100, 317; Angew. Chem. Int. Ed. Engl. 1988, 27, 309.
2. For a review, see G. Maier, Angew. Chem. 1988, 100, 317; Angew. Chem. Int. Ed. Engl. 1988, 27, 309.
3. For recent theoretical papers, see a) M. Balci, M. L. Mckee, P. von R. Schleyer, J. Phys. Chem. A 2000, 104, 1246;
4. b) M. Filatov, S. Shaik, J. Chem. Phys. 1999, 110, 116;
5. c) W. S. S. Wu, Chem. Phys. Lett. 1999, 301, 37;
6. d) R. Redington, J. Chem. Phys. 1998, 109, 10781;
7. e) S. Zilberg, Y. Haas, J. Phys. Chem. A 1998, 102, 10843;
8. f) V. Gogonea, P. von R. Schleyer, P. R. Schreiner, Angew. Chem. 1998, 110, 2045; Angew. Chem. Int. Ed. 1998, 37, 1945;
9. f) V. Gogonea, P. von R. Schleyer, P. R. Schreiner, Angew. Chem. 1998, 110, 2045; Angew. Chem. Int. Ed. 1998, 37, 1945;
10. g) M. N. Glukovtsev, S. Laiter, A. Pross, J. Phys. Chem. 1995, 99, 6828;
11. h) A. Balkova, R. J. Bartlett, J. Phys. Chem. 1994, 101, 8972.
12. W. Watts, J. D. Fitzpatrick, R. Pettit. J. Am. Chem. Soc. 1965, 87, 3253.
13. T. Bally, S. Masamune, Tetrahedran 1980, 36, 343, and references therein.
14. D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024.
15. D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024.
16. a) H. Kimling, A. Krebs, Angew. Chem. 1972, 84, 952; Angew. Chem. Int. Ed. Engl. 1972, 11, 932;
17. a) H. Kimling, A. Krebs, Angew. Chem. 1972, 84, 952; Angew. Chem. Int. Ed. Engl. 1972, 11, 932;
18. b) H. Irngartinger, H. Rodewald, Angew. Chem. 1974, 86, 783; Angew. Chem. Int. Ed. Engl. 1974, 13, 740;
19. b) H. Irngartinger, H. Rodewald, Angew. Chem. 1974, 86, 783; Angew. Chem. Int. Ed. Engl. 1974, 13, 740;
20. c) L. T. J. Delbaere, M. N. G. James, N. Nakamura, S. Masamune, J. Am. Chem. Soc. 1975, 97, 1973;
21. d) G. Maier, S. Pfriem, U. Schäfer, R. Matusch, Angew. Chem. 1978, 90, 552; Angew. Chem. Int. Ed. Engl. 1978, 17, 520;
22. d) G. Maier, S. Pfriem, U. Schäfer, R. Matusch, Angew. Chem. 1978, 90, 552; Angew. Chem. Int. Ed. Engl. 1978, 17, 520;
23. e) H. Irngartinger, N. Riegler, K.-D. Malsch, K.-A. Schneider, G. Maier, Angew. Chem. 1980, 92, 214; Angew. Chem. Int. Ed. Engl. 1980, 19, 211;
24. e) H. Irngartinger, N. Riegler, K.-D. Malsch, K.-A. Schneider, G. Maier, Angew. Chem. 1980, 92, 214; Angew. Chem. Int. Ed. Engl. 1980, 19, 211;
25. f) O. Ermer, E. Heilbronner, Angew. Chem. 1983, 95, 414; Angew. Chem. Int. Ed. Engl. 1983, 22, 402;
26. f) O. Ermer, E. Heilbronner, Angew. Chem. 1983, 95, 414; Angew. Chem. Int. Ed. Engl. 1983, 22, 402;
27. g) H. Irngartinger, M. Nixdorf, Angew. Chem. 1983, 95, 415; Angew. Chem. Int. Ed. Engl. 1983, 22, 403;
28. g) H. Irngartinger, M. Nixdorf, Angew. Chem. 1983, 95, 415; Angew. Chem. Int. Ed. Engl. 1983, 22, 403;
29. h) G. Maier, R. Emrich, K.-D. Malsch, K.-A. Schneider, M. Nixdorf, H. Irngartinger, Chem. Ber. 1985, 118, 2798;
30. i) J. D. Dunitz, C. Krüger, H. Irngartinger, E. F. Maverick, Y. Wang, M. Nixdorf, Angew. Chem. 1988, 100, 415; Angew. Chem. Int. Ed. Engl. 1988, 27, 387;
31. i) J. D. Dunitz, C. Krüger, H. Irngartinger, E. F. Maverick, Y. Wang, M. Nixdorf, Angew. Chem. 1988, 100, 415; Angew. Chem. Int. Ed. Engl. 1988, 27, 387;
32. j) H. Irngartinger, M. Nixdorf, N. H. Riegler, A. Krebs, H. Kimling, J. Pocklington, G. Maier, K.-D. Malsch, K.-A. Schneider, Chem. Ber. 1988, 121, 673;
33. k) H. Irngartinger, M. Nixdorf, Chem. Ber. 1988, 121, 679;
34. l) G. Maier, D. Born, Angew. Chem. 1989, 101, 1085; Angew. Chem. Int. Ed. Engl. 1989, 28, 1050;
35. l) G. Maier, D. Born, Angew. Chem. 1989, 101, 1085; Angew. Chem. Int. Ed. Engl. 1989, 28, 1050;
36. m) G. Maier, F. Fleischer, Tetrahedron Lett. 1991, 32, 57;
37. n) G. Maier, D. Born, I. Bauer, R. Wolf, R. Boese, D. Cremer, Chem. Ber. 1994, 127, 173;
38. o) G. Maier, R. Wolf, H.-O. Kalinowski, R. Boese, Chem. Ber. 1994, 127, 191;
39. p) G. Maier, R. Wolf, H.-O. Kalinowski, Chem. Ber. 1994, 127, 201;
40. q) G. Maier, H. Rang, R. Emrich, Liebigs Ann. 1995, 153;
41. r) G. Maier, H. Rang, R. Emrich, H. Irngartinger, Liebigs Ann. 1995, 161;
42. s) G. Maier, F. Fleischer, Liebigs Ann. 1995, 169;
43. t) G. Maier, H. Rang, F. Fleischer, H.-O. Kalinowski, Liebigs Ann. 1995, 173.
44. G. Maier, H. W. Lage, H. P. Reisenauer, Angew. Chem. 1981, 93, 1010; Angew. Chem. Int. Ed. Engl. 1981, 20, 976.
45. G. Maier, H. W. Lage, H. P. Reisenauer, Angew. Chem. 1981, 93, 1010; Angew. Chem. Int. Ed. Engl. 1981, 20, 976.
46. a) A. Sekiguchi, T. Matsuo, H. Watanabe, J. Am. Chem. Soc. 2000, 122, 5652;
47. b) T. Matsuo, T. Mizue, A. Sekiguchi, Chem. Lett. 2000, 896.
48. 6]benzene, TMS): δ = 11.0, - 3.2.
49. Preliminary X-ray diffraction analysis of 2 at 120 K showed a rectangular structure for the cyclobutadiene ring. However, the refinement was unsatisfactory as a result of the poor quality of the crystals.
50. 1]chloroform, TMS): δ = - 9.0.
51. 8]toluene, TMS): δ = - 5.1.
52. o). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-152460. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+ 44)1223-336-033: e-mail: deposit@ccdc.cam. ac.uk).
53. E. Kloster-Jensen, G. A. Eliassen, Angew. Chem. 1985, 97, 587; Angew. Chem. Int. Ed. Engl. 1985, 24, 565.
54. E. Kloster-Jensen, G. A. Eliassen, Angew. Chem. 1985, 97, 587; Angew. Chem. Int. Ed. Engl. 1985, 24, 565.
55. An alternative way to 2 is: G. Maier, J. Neudert, O. Wolf, Angew. Chem. 2001, 113, 1719; Angew. Chem. Int. Ed. 2001, 40, 1674, previous communication.
56. An alternative way to 2 is: G. Maier, J. Neudert, O. Wolf, Angew. Chem. 2001, 113, 1719; Angew. Chem. Int. Ed. 2001, 40, 1674, previous communication.