Convenient access to monosilicon epoxides with pentacoordinate silicon

Angewandte Chemie - International Edition

Volumn 49, Issue 23, 2010, Pages 3952-3955

  Ghadwal, Rajendra S ^a   Sen, Sakya S ^a   Roesky, Herbert W ^a   Granitzka, Markus ^a   Kratzert, Daniel ^a   Merkel, Sebastian ^a   Stalke, Dietmar ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Carbene ligands; Cycloaddition; Heterocycles; Silicon; Small ring systems

Indexed keywords

CARBENE LIGANDS; CHEMICAL EQUATIONS; CYCLOADDITION REACTION; HETEROCYCLES; LEWIS BASE; PENTACOORDINATE SILICON; RING SYSTEMS; THREE-MEMBERED RINGS; X-RAY DIFFRACTION STUDIES;

CHLORINE COMPOUNDS; CYCLOADDITION; ENERGY ABSORPTION; KETONES; O RINGS; REACTION INTERMEDIATES; X RAY DIFFRACTION;

LIGANDS;

EID: 77953019529     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201000835     Document Type: Article

References (77)

1. D. M. Hodgson, C. D. Bray in Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006, chap. 5, pp. 145-184;
2. H. Adolfsson, D. Balan in Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), WileyVCH, Weinheim, 2006, chap. 6, pp. 185-228;
3. L. P. C. Nielsen, E. N. Jacobsen in Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006, chap. 7, pp. 229-269;
4. P. Crotti, M. Pineschi in Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006, chap. 8, pp. 271-313;
5. B. Olofsson, P. Somfai in Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), WileyVCH, Weinheim, 2006, chap. 9, pp. 315-347;
6. S. Grüschow, D. H. Sherman in Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006, chap. 10, 349-398;
7. V. V. Fokin, P. Wu in Aziridines and Epoxides in Organic Synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006, chap. 2, pp. 443-447.
8. a) P. P. Gaspar, R. West in the Chemistry of Organic Silicon Compounds, Vol. 2 (Eds.: Z. Rappoport, Y. Apeloig), Wiley, New York, 1998, pp. 2463-2568;
9. b) M. Haff, T. A. Schmedake, R. West, Acc. Chem. Res. 2000, 33, 704-714;
10. c) N. J. Hill, R. West, J. Organomet. Chem 2004, 689, 4165-4183;
11. d) B. Gehrhus, P. B. Hitchcock, R. Pongtavornpinyo, L. Zhang, J. Chem. Soc. Dalton Trans. 2006, 1847-1857.
12. a) S. W. Benson, Thermochemical Kinetics, 2nd ed., Wiley, New York, 1976, pp. 60-63;
13. b) M. Driess, H. Grützmacher, Angew. Chem. 1996, 108, 900-929;
14. Angew. Chem. Int. Ed. Engl. 1996, 35, 828-856.
15. a) M. Ishikawa, K. Nishimura, H. Sugisawa, M. Kumada, J. Organomet. Chem. 1980, 194, 147-158;
16. b) M. Ishikawa, H. Sugisawa, T. Fuchikami, M. Kumada, T. Yamabe, H. Kawakami, K. Fukui, Y. Ueki, H. Shizuka, J. Am. Chem. Soc. 1982, 104, 2872-2878;
17. c) M. Ishikawa, H. Sugisawa, M. Kumada, T. Higuchi, K. Matsui, K. Hirotsu, Organometallics 1982, 1, 1473-1477;
18. d) D. Seyferth, M. L. Shannon, S. C. Vick, T. F. O. Lim, Organometallics 1985, 4, 57-62;
19. e) M. Ishikawa, T. Horio, Y. Yuzuriha, A. Kunai, T. Tsukihara, H. Naitou, Organometallics 1992, 11, 597-601;
20. f) A. Kunai, Y. Matsuo, J. Ohshita, M. Ishikawa, Y. Aso, T. Otsubo, F. Ogura, Organometallics 1995, 14, 1204-1212;
21. g) W. Ando, T. Shiba, T. Hidaka, K. Morihashi, O. Kikuchi, J. Am. Chem. Soc. 1997, 119, 3629-3630;
22. h) A. Kunai, T. Mihara, Y. Matsuo, J. Ohshita, A. Naka, M. Ishikawa, J. Organomet. Chem. 1997, 545-546, 611-613;
23. i) S. Tsutsui, K. Sakamoto, M. Kira, J. Am. Chem. Soc. 1998, 120, 9955-9956;
24. j) A. Sekiguchi, M. Ichinohe, S. Yamaguchi, J. Am. Chem. Soc. 1999, 121, 10231-10232;
25. k) M. Takahashi, S. Tsutsui, K. Sakamoto, M. Kira, T. Müller, Y. Apeloig, J. Am. Chem. Soc. 2001, 123, 347-348;
26. I) M. Ichinohe, T. Tanaka, A. Sekiguchi, Chem. Lett. 2001, 1074-1075;
27. m) J. Ohshita, N. Honda, K. Nada, T. Iida, T. Mihara, Y. Matsuo, A. Kunai, A. Naka, M. Ishikawa, Organometallics 2003, 22, 2436-2441;
28. n) S. Yao, C. van Wüllen, X.-Y. Sun, M. Driess, Angew. Chem. 2008, 120, 3294-3297;
29. Angew. Chem. Int. Ed. 2008, 47, 3250-3253;
30. Angew. Chem. 2008, 120, 3294-3297.
31. a) M. Ishikawa, T. Fuchikami, M. Kumada, J. Am. Chem. Soc. 1977, 99, 245-247;
32. b) H. Sakurai, Y. Kamiyama, Y. Nakadaira, J. Am. Chem. Soc. 1977, 99, 3879-3880;
33. c) K. Sakamoto, S. Tsutsui, H. Sakurai, M. Kira, Bull. Chem Soc. Jpn. 1997, 70, 253-260;
34. d) J. Hermanns, B. Schmidt, J. Chem. Soc. Perkin Trans. 1 1998, 2209-2230;
35. e) N. Takeda, N. Tokitoh, R. Okazaki, Chem. Lett. 2000, 622-623.
36. a) H. B. Schlegel, P. N. Skancke, J. Am. Chem. Soc. 1993, 115, 10916-10924;
37. b) N. H. Morgon, A. B. Argenton, M. L. P. da Silva, J. M. Riveros, J. Am. Chem Soc. 1997, 119, 1708-1716;
38. c) R. Becerra, J. P. Cannady, R. Walsh, J. Phys Chem. A 1999, 103, 4457-4464;
39. d) H. Ikeda, S. Inagaki, J. Phys. Chem. A 2001, 105, 10711-10718;
40. e) C. Tian, H. Yu, X. Lu, THEOCHEM 2008, 861, 39-45;
41. f) X. H. Lu, H. B. Yu, X. Che, P. P. Xiang, Int. J. Quantum Chem 2008, 108, 1114-1122.
42. a) W. Ando, M. Ikeno, A. Sekiguchi, J. Am Chem. Soc 1977, 99, 6447-6449;
43. b)M. Ishikawa, K.-I. Nakagawa, M. Kumada, J. Organomet. Chem. 1977, 135, C45-C49;
44. c) W. Ando, M. Ikeno, A. Sekiguchi, J. Am. Chem. Soc. 1978, 100, 3613-3615;
45. d) D. Seyferth, T. F. O. Lim, J. Am. Chem. Soc. 1978, 100, 7074-7075;
46. e) A. Schäfer, M. Weidenbruch, S. Pohl, J. Organomet. Chem. 1985, 282, 305-313;
47. f) W. Ando, K. Hagiwara, A. Sekiguchi, Organometallics 1987, 6, 2270-2271;
48. g) J. Belzner, H. Ihmels, L. Pauletto, J. Org. Chem. 1996, 61, 3315-3319;
49. h) N. Sakai, T. Fukushima, S. Minakata, I. Ryu, M. Komatsu, Chem. Commun. 1999, 1857-1858;
50. i) A. K. Franz, K. A. Woerpel, J. Am. Chem. Soc. 1999, 121, 949-957;
51. j) N. Sakai, T. Fukushima, A. Okada, S. Ohashi, S. Minakata, M. Komatsu, J. Organomet. Chem. 2003, 686, 368-372;
52. k) S. A. Calad, K. A. Woerpel, J. Am. Chem. Soc. 2005, 127, 2046-2047;
53. l) S. A. Calad, K. A. Woerpel, Org. Lett. 2007, 9, 1037-1040;
54. m) B. E. Howard, K. A. Woerpel, Org. Lett. 2007, 9, 4651-4653;
55. n) L. E. Bourque, K. A. Woerpel, Org. Lett. 2008, 10, 5257-5260;
56. o) M. Prévost, K. A. Woerpel, J. Am. Chem. Soc. 2009, 131, 14182-14183.
57. a) P. Jutzi, D. Eikenberg, E.-A. Bunte, A. Möhrke, B. Neumann, H.-G. Stammler, Organometallics 1996, 15, 1930-1934;
58. b) B. Gehrhus, P. B. Hitchcock, M. F. Lappert, Organometallics 1997, 16, 4861-4864;
59. c) B. Gehrhus, M. F. Lappert, Polyhedron 1998, 17, 999-1000;
60. d) Y. Xiong, S. Yao, M. Driess, Chem. Eur. J. 2009, 15, 5545-5551.
61. W. Ando, Y. Hamada, A. Sekiguchi, Tetrahedron Lett. 1982, 23, 5323-5326.
62. R. S. Ghadwal, H. W. Roesky, S. Merkel, J. Henn, D. Stalke, Angew. Chem. 2009, 121, 5793-5796;
63. Angew. Chem. Int Ed. 2009, 48, 5683-5686;
64. Angew. Chem. 2009, 121, 5793-5796.
65. a) C.-W. So, H. W. Roesky, J. Magull, R. B. Oswald, Angew. Chem. 2006, 118, 4052-4054;
66. Angew. Chem. Int. Ed. 2006, 45, 3948-3950;
67. Angew. Chem. 2006, 118, 4052-4054;
68. b) S. S. Sen, H. W. Roesky, D. Stern, J. Henn, D. Stalke, J. Am. Chem. Soc. 2010, 132, 1123-1126.
69. a) J. A. Hawari, D. Griller, Organometallics 1984, 5, 1123-1124;
70. b) J. Heinicke, B. Gehrhus, J. Organomet. Chem. 1992, 423, 13-21;
71. c) J. Heinicke, S. Meinel, J. Organomet. Chem. 1998, 561, 121-129;
72. d) A. Naka, M. Ishikawa, J. Organomet. Chem. 2003, 685, 162-167.
73. Crystallographic details: A shock-cooled crystal was selected and mounted under nitrogen atmosphere by using X-TEMP2 (T. Kottke, D. Stalke, J. Appl. Crystallogr. 1993, 26, 615-619;
74. D. Stalke, Chem. Soc. Rev. 1998, 27, 171-178).
75. 1/c, a = 15.947(2), b = 12.9563(15), c = 36.133(5) Å, β = 93.878(2)°, wR2 = 0.1135, R1 = 0.0451.
76. a) N. Kuhn, T. Kratz, D. Bläser, R. Boese, Chem. Ber. 1995, 128, 245-250;
77. b) Y. Takeuchi, T. Takayama in The Chemistry of Organic Silicon Compounds, Vol. 2 (Eds.: Z. Rappoport, Y. Apeloig), Wiley, New York, 1998, pp. 267 - 354.