Intramolecular Se ⋯ N nonbonding interactions in low-valent organoselenium derivatives: A detailed study by 1H and 77Se NMR spectroscopy and X-ray crystallography

Chemistry - A European Journal

Volumn 5, Issue 5, 1999, Pages 1411-1421

  Mugesh, G ^a   Panda, Arunashree ^a   Singh, Harkesh B ^a   Butcher, Ray J ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b HOWARD UNIVERSITY   (United States)

Author keywords

Halides; Hypervalent compounds; Intramolecular coordination; Selenides; Selenium

Indexed keywords

EID: 85088082169     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19990503)5:5<1411::aid-chem1411>3.3.co;2-d     Document Type: Article

References (97)

1. a) H. Fujihara, H. Mima, T. Erata, N. Furukawa, J. Chem. Soc. Chem. Commun. 1991, 98;
2. b) H. Fujihara, M. Yabe, J.-J. Chiu, N. Furukawa, Tetrahedron Lett. 1991, 32, 4345;
3. c) H. Fujihara, H. Mima, N. Furukawa, J. Am. Chem. Soc. 1995, 117, 10153;
4. d) H. Fujihara, T. Uehara, N. Furukawa, J. Am. Chem. Soc. 1995, 117, 6388;
5. e) H. Fujihara, H. Tanaka, N. Furukawa, J. Chem. Soc. Perkin Trans. 2 1995, 2375;
6. f) M. Iwaoka, S. Tomoda, J. Org. Chem. 1995, 60, 5299;
7. g) H. Fujihara, H. Tanaka, N. Furukawa, J. Chem. Soc. Perkin Trans. 2 1995, 2375;
8. h) M. Iwaoka, H. Komatsu, S. Tomoda, Bull. Chem. Soc. Jpn. 1996, 69, 1828;
9. i) W. Nakanishi, S. Hayashi, S. Toyota, Chem. Commun. 1996, 371;
10. j) W. Nakanishi, S. Hayashi, A. Sakaue, G. Ono, Y. Kawada, J. Am. Chem. Soc. 1998, 120, 3635.
11. a) T. Wirth, K. J. Kulicke, G. Fragle, Helv. Chim. Acta 1996, 79, 1957;
12. b) K. Fujita, Rev. Heteroatom. Chem. 1997, 16, 101;
13. c) T. Wirth, Liebigs Ann. Chem. 1997, 2189;
14. d) T. Wirth, G. Fragale, Chem. Eur. J. 1997, 3, 1894;
15. e) T. Wirth, G. Fragale, M. Spichty, J. Am. Chem. Soc. 1998, 120, 3376;
16. f) R. Déziel, S. Goulet, L. Grenier, J. Bordeleau, J. Bernier, J. Org. Chem. 1993, 58, 3619;
17. g) R. Déziel, E. Malenfant, J. Org. Chem. 1995, 60, 4660;
18. h) R. Déziel, E. Malenfant, C. Thibault, S. Frechette, M. Gravel, Tetrahedron Lett. 1997, 38, 4753;
19. i) S. Fukuzawa, Y. Kasugahara, S. Uemura, Tetrahedron Lett. 1994, 35, 9403;
20. j) Y. Nishibayashi, J. D. Singh, S. Uemura, S. Fukuzawa, Tetrahedron Lett. 1994, 35, 3115;
21. k) Y. Nishibayashi, J. D. Singh, K. Sagawa, S. Fukuzawa, S. Uemura, J. Chem. Soc. Chem. Commun. 1994, 1375;
22. l) Y. Nishibayashi, J. D. Singh, S. Uemura, Tetrahedron Lett. 1994, 35, 3115;
23. m) Y. Nishibayashi, J. D. Singh, S. Fukuzawa, S. Uemura, J. Org. Chem. 1995, 60, 4114;
24. n) Y. Nishibayashi, J. D. Singh, S. Fukuzawa, S. Uemura, J. Chem. Soc. Perkin Trans. 1 1995, 2871;
25. o) Y. Nishibayashi, T. Chiba, K. Ohe, S. Uemura, J. Chem. Soc. Chem. Commun. 1995, 1243;
26. p) T. Chiba, Y. Nishibayashi, J. D. Singh, K. Ohe, S. Uemura, Tetrahedron Lett. 1995, 36, 1519;
27. q) Y. Nishibayashi, S. K. Srivastava, H. Takada, S. Fukuzawa, S. Uemura, J. Chem. Soc. Chem. Commun. 1995, 2321;
28. r) Y. Nishibayashi, K. Segawa, J. D. Singh, S. Fukuzawa, K. Ohe, S. Uemura, Organometallics 1996, 15, 370;
29. s) K. Fujita, K. Murata, M. Iwaoka, S. Tomoda, Tetrahedron Lett. 1995, 36, 5219;
30. t) K. Fujita, K. Murata, M. Iwaoka, S. Tomoda, J. Chem. Soc. Chem. Commun. 1995, 1641;
31. u) K. Fujita, K. Murata, M. Iwaoka, S. Tomoda, Tetrahedron 1997, 53, 2029.
32. a) M. Iwaoka, S. Tomoda, J. Chem. Soc. Chem. Commun. 1992, 1165;
33. b) K. Fujita, M. Iwaoka, S. Tomoda, Chem. Lett. 1994, 923;
34. c) T. Wirth, Tetrahedron Lett. 1995, 36, 7849;
35. d) R. Kaur, H. B. Singh, R. P. Patel, J. Chem. Soc. Dalton Trans. 1996, 2719;
36. e) S. Fukuzawa, K. Takahashi, H. Kato, H. Yamazaki, J. Org. Chem. 1997, 62, 7711;
37. f) T. Wirth, S. Hauptli, M. Leuenberger, Tetrahedron Asymmetry 1998, 9, 547.
38. a) Y. Cheng. T. J. Emge, J. G. Brennan, Inorg. Chem. 1994, 33, 3711;
39. b) Y. Cheng, T. J. Emge, J. G. Brennan, Inorg. Chem. 1996, 35, 3342;
40. c) Y. Cheng. T. J. Emge, J. G. Brennan, Inorg. Chem. 1996, 35, 7339;
41. d) R. Kaur, H. B. Singh, R. P. Patel, S. K. Kulshreshtha, J. Chem. Soc. Dalton Trans. 1996, 461;
42. e) G. Mugesh, H. B. Singh, R. P. Patel, R. J. Butcher, Inorg. Chem. 1998, 37, 2663.
43. a) S. R. Wilson, P. A. Zucker, R.-R. C. Huang, A. Spector, J. Am. Chem. Soc. 1989, 111, 5936;
44. b) A. Spector, S. R. Wilson, P. A. Zucker, US 5, 321, 138 (Cl. 546-224; C07C37/02) 1994; Chem. Abstr. 1994, 121, P256039r;
45. c) L. Engman, D. Stern, I.A. Cotgreave, C.M. Andersson, J. Am. Chem. Soc. 1992, 114, 9737;
46. d) V. Galet, J.-L. Bernier, J.-P. Henichart, D. Lesieur, C. Abadie, L. Rochelte, A. Lindenbaum, J. Chalas, J.-F. R. Faverie, B. Pfeiffer, P. Renard, J. Med. Chem. 1994, 37, 2903;
47. e) M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1994, 116, 2557;
48. f) T. Saiki, K. Goto, R. Okazaki, Angew. Chem. 1997, 109, 2320; Angew. Chem. Int. Ed. Engl. 1997, 36, 2223.
49. f) T. Saiki, K. Goto, R. Okazaki, Angew. Chem. 1997, 109, 2320; Angew. Chem. Int. Ed. Engl. 1997, 36, 2223.
50. N. Ramasubbu, R. Parthasarathy, Phosphorus Sulfur 1987, 31, 221.
51. B. M. Goldstein, S. D. Kennedy, W. J. Hennen, J. Am. Chem. Soc. 1990, 112, 8285.
52. D. H. R. Barton, M. B. Hall, Z. Lin, S. I. Parekh, J. Reibenspies, J. Am. Chem. Soc. 1993, 115, 5056.
53. 77Se NMR Chemical Shifts, Wiley, Chichester, 1996;
54. b) M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1996, 118, 8077.
55. a) H. B. Singh, N. Sudha, A. A. West, T A. Hamor, J. Chem. Soc. Dalton Trans. 1990, 807;
56. b) H. B. Singh, N. Sudha, R. J. Butcher, Inorg. Chem. 1992, 31, 1431;
57. c) N. Sudha, H. B. Singh, Coord. Chem. Rev. 1994, 135/136, 469;
58. d) V. A. Regini, R. Kaur, N. Sudha, S. C. Menon, H. B. Singh, Proc. Indian Acad. Sci. Chem. Sci. 1995, 107, 431;
59. e) R. Kaur, H. B. Singh, R. J. Butcher, Organometallics 1995, 14, 4755;
60. f) S. C. Menon, H. B. Singh, J. M. Jasinski, J. P. Jasinski, R. J. Butcher, Organometallics 1996, 15, 1707;
61. g) S. C. Menon, H. B. Singh, R. P. Patel, K. Das, R. J. Butcher, Organometallics 1997, 18, 563.
62. G. Mugesh, A. Panda, H. B. Singh, N. S. Punekar, R. J. Butcher, Chem. Commun. 1998, 2227.
63. M. R. Detty, A. E. Friedman, M. McMillan, Organometallics 1994, 13, 3338.
64. H. D. Maddox, J. D. McCullough, Inorg. Chem. 1966, 5, 522.
65. T. Klapotke, J. Passmore, Acc. Chem. Res. 1989, 22, 234.
66. W. W. Du Mont, S. Kubiniok, K. Peters, H. Von Schnering, Angew. Chem. 1987, 99, 820; Angew. Chem. Int. Ed. Engl. 1987, 26, 780.
67. W. W. Du Mont, S. Kubiniok, K. Peters, H. Von Schnering, Angew. Chem. 1987, 99, 820; Angew. Chem. Int. Ed. Engl. 1987, 26, 780.
68. W. W. Du Mont, A. Martens, S. Pohl, W. Saak, Inorg. Chem. 1990, 29, 4847.
69. C. W. Perkins, J. S. Martins, J. Am. Chem. Soc. 1980, 102, 1155.
70. H. Higuchi, M. Kugimiya, T. Otsubo, Y. Sakata, S. Misumi, Tetrahedron Lett. 1983, 24, 2593.
71. M. C. Fong, C. H. Schiesser, J. Org. Chem. 1997, 62, 3103.
72. C. H. Schiesser, K. Sutej, J. Chem. Soc. Chem. Commun. 1992, 57.
73. C. H. Schiesser, K. Sutej, Tetrahedron Lett. 1992, 33, 5137.
74. E. G. Hope, W. Levason, J. Chem. Soc. Perkin Trans. 2 1984, 429.
75. H. Fujihara, H. Mima, T. Erata, N. Furukawa, J. Am. Chem. Soc. 1992, 114, 3117.
76. M. Iwaoka, S. Tomoda, Phosphorus Sulfur Silicon 1992, 67, 125.
77. W. McFarlane, R. J. Wood, J. Chem. Soc. A. 1972, 1397.
78. M. Iwaoka, S. Tomoda, J. Org. Chem. 1995, 60, 5299.
79. H. Fujihara, H. Mima, N. Furukawa, J. Am. Chem. Soc. 1995, 117, 10153.
80. C. K. Johnson, ORTEP II; Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN (USA), 1976.
81. H. Fujihara, H. Mima, M. Ikemori, N. Furukawa, J. Am. Chem. Soc. 1991, 113, 6337.
82. S. M. Goldfrey, C. A. McAuliffe, R. G. Pritchard, S. Sarwar, J. Chem. Soc. Dalton Trans. 1997, 1031.
83. L. Pauling, The Nature of the Chemical Bond, 3rd ed., Cornell University Press, Ithaca, New York, 1960, p. 224.
84. M. Baiwir, G. Llabres, O. Dideberg, L. Dupont, J. L. Piette, Acta Crystallogr. Sect. B, 1975, 31, 2188.
85. W. A. S. Nandana, J. Passmore, P. S. White, C.-M. Wong, J. Chem. Soc. Chem. Commun. 1982, 1098.
86. W. Behrendt, U. W. Gerwarth, S. Jager, I. Kreuzbichler, K. Seppelt, Gmelin Handbook of Organic Chemistry, 8th ed., Selenium Supplement, Vol. B2, Springer, Berlin, 1984, p. 272.
87. S. A. Mbogo, W. R. McWhinnie, T. S. Lobana, J. Organomet. Chem. 1990, 388, 273.
88. W. Baratta, P. S. Pregosin, A. Bacchi, G. Pelizzi, Inorg. Chem. 1994, 33, 4494.
89. D. L. Eng-Wilmot, D. van der Helm, J. Am. Chem. Soc. 1980, 102, 7719.
90. R. Jaunin, W. E. Oberhansli, J. Hellerbach, Helv. Chim. Acta 1972, 55, 2975.
91. a) A. Panda, G. Mugesh, H. B. Singh, R. J. Butcher, Organometallics, 1999 in press;
92. b) G. Mugesh, H. B. Singh, R. J. Butcher, Tetrahedron: Asymmetry 1999, 10, 237.
93. D. D. Perrin, W. L. F. Armargo, D. R. Perrin, Purification of Laboratory Chemicals, Pergamon, New York, 1980.
94. J. Zavada, M. Pankova, P. Holy, M. Tichy, Synthesis 1994, 11, 1132.
95. G. M. Sheldrick, SHELXS-86, Program for the Solution of Crystal Structures, University of Göttingen, 1986.
96. G. M. Sheldrick, SHELXL-93, A Program for Refining Crystal Structures, University of Göttingen, 1993.
97. International Tables for X-Ray Crystallography 1, Kynoch, Birmingham, 1974, pp. 99, 149.