Syntheses and X-ray crystal-structure analyses of trifluoromethyl-substituted ketiminodiselanes, selenoamides and selenoacrylamides

Chemische Berichte

Volumn 130, Issue 7, 1997, Pages 913-922

  Hanne Blau, Joseph Grobe ^a   Van Le, Duc ^a   Krebs, Bernt ^a   Läge, Mechthild ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Amides; Cleavage reactions; Cycloadditions; Fluorine; Selenium

Indexed keywords

EID: 0009350993     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300717     Document Type: Article

References (103)

1. J. Grobe, D. Le Van, F. Immel, B. Krebs, M. Läge, Cliem. Ber. 1996,729, 1271-1274.
2. Raj A Ogawa, N. Sonoda in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, vol. 6, pp. 476-484.
3. [2b] F. S. Guziec, Jr. in Organoselenium Chemistry (Eds.: D. Liotta), Wiley, New York, 1987, pp. 277-324.
4. [2c] C. Paulmier in Selenium Reagents and Intermediates in Organic Synthesis (Eds.: J. E. Baldin), Pergamon Press, Oxford, 1986, pp. 58-83.
5. [3a] T. Murai, T. Ezaka, N. Niwa, T. Kanda, S. Kalo, Synlett 1996, 865-866.
6. [3b] K. Shimada, S. Akimoto, H. Itoh, H. Nakamura, Y. Takikawa, Cliem. Lett. 199-4, 1743-1746.
7. [3c] H. Ishihara, M. Yoshimi, S. Kalo, Angew. Chem. 1990, 702, 572-573,
8. Angew. Chem. Int. Ed. Engl 1990, 29, 530-531.
9. [4a] H. Fischer, A. Tiriliomis, U. Gerbing, B. Huber, G. Müller, J. Chem. Soc., Chem. Commun. 1987, 559-560.
10. [4b] H. Fischer, U. Gerbing, A. Tiriliomis, G. Müller, B. Huber, J. Riede, J. Hofmann, P. Burger, Chem. Ber. 1988, 727, 2095-2102.
11. [4c] H. Fischer, J. Hofmann, U. Gerbing, A. Tiriliomis, J. Organomet. Chem. 1988, 358, 229-244.
12. J. Nakayama, A. Mizumura, I. Akiyama, T. Nishio, I. lida, Chem. Lett. 1994, 77-80.
13. K. Shimada, S. Hikaee, Y. Takeishi, Y. Takikawa, Chem. Lett. 1990, 1403-1406.
14. [7a] M.-D. Ruan, p.-F zhang, Y. Tao, W.-Q. Fan, Synth. Commun. 1996, 26, 2617-2623.
15. [7b] L.-L. Lai, D. H. Reid, Synthesis 1993, 870-872.
16. [7c] D. Dubreuil, J. P. Pradére, N. Gireaudeau, M. Goli, F. Tonnard, Tetrahedron Lett. 1995, 36, 237-240.
17. [8a] K okuma, K. Ikari, H. Ohta, Chem. Lett. 1992, 131-134.
18. [8b] Y. Takikawa, M. Yamaguchi, T. Sasaki, K. Ohnishi, K. Shimada, Chem. Lett. 1994, 2105-2108.
19. [8c] D.-L. An, K. Toyota, M. Yasunami, M. Yoshifuji, Chem. Lett. 1995, 199-200.
20. [8d] K. Shimada, M. Yamaguchi, T. Sasaki, K. Ohnishi, Y. Takikawa, Bull. Chem. Soc. Jpn. 1996, 69, 2235-2242.
21. [9a] T. Murai, T. Mizutani, T. Kanda, S. Kalo, Heteroatom. Chem. 1995, 6, 241-246.
22. [9b] P. A. Otten, S. Gorter, A. van der Gen, Chem. Ber. 1997, 130, 49-54.
23. [10a] A. Haas, J. Fluorine Chem. 1986, 32, 415-439.
24. [10b] J. Grobe, D. Le Van, Angew. Chem. 1984, 96, 716-717; Angew. Chem. Int. Ed. Engl. 1984, 23, 710-711.
25. A. Haas, M. Spehr, Chimia 1988, 42, 265-267.
26. [12a] J. Grobe, D. Le Van, J. Welzel, J. Organomet. Chem. 1988, 340, 153-160
27. [12b] J. Grobe, D. Le Van, J. Welzel, J. Organomet. Chem. 1990,556, 321-332.
28. [13a] R. Boese, A. Haas, M. Spehr, Chem. Ber. 1991, 724, 51-61.
29. [13bl A. Haas, C. Limberg, M. Spehr, Chem. Ber. 1991, 124, 423-426.
30. G. Rabe, K. Keller, H. W. Roesky, R. J. Laeow, F. Pauer, D. Stalke, Z. Naturforsch., B: Chem. Sei. 1991, 46, 157-160.
31. H. Blau, J. Grobe, D. Le Van, H.-G. Mack, H. Oberhammer, C/iem. Der. 1994, 127, 647-650.
32. P. Dehnert, J. Grobe, D. Le Van, Z. Naturforscli., B: Anorg. Chem., Org. Cliem. 1981, 36, 48-54.
33. [17a] J. Grobe, R Rall; J Fluorine Client. 1978, 77, 265-290.
34. [17b] J. Grobe, R. Haubold, Z. Anorg. Allg. Chem. 1985, 522, 159-170.
35. G. Klöter, K. Seppelt, J. Am. Chan. Soc. 1979, 707, 347-349.
36. W. J. Middleton, E. G. Howard, W. H. Sharkey, J. Org. Chem. 1965,50, 1375-1384.
37. [20a] J. Grobe, D. Le van, J. Nientiedt, B. Krebs, M. Dartmann, Chem. Ber. 1988,121, 655-664.
38. [20b] J. Grobe, D. Le Van, B. Lüth, M. Hecemann, Chem. Ber. 1990, 123, 2317-2320.
39. [20c] J. Grobe, D. Le Van, U. Althoff, B. Krebs, M. Dartmann, R. Gleiter, Heteroatom Chem. 1991, 2, 385-394.
40. [20d] J. Grobe, D. Le Van, G. Lange, Z. Naturforscli., B: Chem. Sei. 1993, 48, 58-67.
41. T. Albers, J. Grobe, D. Le Van, B. Krebs, M. Läee, Z. Naturforsch.. B: Chem. Sei. 1995, 50, 94-100.
42. [22a] V. P. Rao, chandrasekhar, V. Ramamurthy, J. Chem. Soc., Perkin Trans. 2 1988, 647-659.
43. [22b] H. Bock, S. Aygen, P. Rosmus, B. Solouki, E. Weißfloe, Chem. Ber. 198-4, 117, 187-202.
44. [22c] S. Collins, T. G. Back, A. Rauk, J. Am. Chem. Soc. 1985, 707, 6589-6592.
45. D. L. Boger, S. M. Weinreb in Organic Chemistry (Ed.: H. H. Wassermann), vol. 47, Academic Press, Inc., New York, 1987, pp. 120-145.
46. [24a] T. G Backi D. R. H. Barton, M. R. Britten-Kelly, F. S. Guziec, Jr., J. Chem. Soc., Perkin Trans, l 1976, 2079-2089.
47. [24b] A. Krebs, W. Rueer, W. U. Nickel, Tetrahedron Lett. 1981, 22, 4937-4940.
48. W. J. Middleton, J. Org. Chem. 1965, 30, 1390-1398.
49. [26a] A. Darmadi, A. Haas, B. Koch, Z. Naturforscli. B: Anorg. Chem., Org. Chem. 1980, 55, 526-529.
50. [26b] I R. Boese, A. Haas, C. Limbere, J. Chem. Soc., Dalton Trans. 1993, 2547-2556.
51. [27a] E. R. Cullen,.R. S. Guziec, Jr., C. J. Murphy, J. Org. Chem. 1982, 47, 3563-3566.
52. [27b] S. Watanabe, T. Kawashima, R. Okazaki, Chem. Lett. 1994, 1289-1292.
53. [28a] P. T. Meinke, G. A. Krafft, J. Am. Chem. Soc. 1988, 110, 8679-8685.
54. [28b] N. Takeda, N. Tokitoh, R. Okazaki, Angew. Chem. 1996, 705, 714-716; Angew. Chem. Int. Ed. Engl. 1996, 55, 660-662.
55. [29a] G. A. Krafft, P. T. Meinke, J. Am. Chem. Soc. 1986, 705, 1314-1315.
56. [29b] G. W. Kirby, A. N. Tretheway, J. Chem. Soc., Chem. Commun. 1986, 1152-1154.
57. [29c] H. Fischer, U. Gerbine, J. Riede, R. Benn, Angeu: Chem. 1986, 98, 80-81; Angew. Chem. Int. Ed. Engl. 1986,25, 78-79.
58. [29d] H. Fischer, U. Gerbina, J. Riede, J. Organomet. Chem. 1989, 364, 155-167.
59. [29e] G. Erker, R. Hock, C. Krüger, S. Werner, F. G. Klärer, U. Artschwager-Perl, Augen: Chem. 1990,702, 1082-1084; Angew. Chem. Int. Ed. Engl. 1990, 29, 1067-1069.
60. [29f] K. Okuma, Y. Komiya, I. Kaneko, Y. Tachibana, E. Iwata, H. Ohta, Bull. Chem. Soc. Jpn. 1990, 63, 1653-1657.
61. [29g] M. Segi, S. Kato, T. Nakajima, Tedrahedron Lett. 1991,32, 7427-7430.
62. [29h] R. Hock, S. Hillebrand, G. Erker, C. Krüger, S. Werner, Client. Ber. 1993, 726, 1895-1903.
63. [29i] K. Shfmada, S. Akimoto, Y. Takikawa, C. Kabuto, Chem. Lett. 1994, 2283-2286.
64. [29j] S. Wilke, G. Erker, J. Am. Chem. Soc. 1995, 777, 10922-10930 and references cited therein.
65. N. P. Luthra, J. D. Odom in The Chemistry of Organic Selenium and Tellurium Compounds, vol. 1 (Eds.: S. Patai, Z. Rappoport), John Wiley & Sons, New York, 1986, pp. 189-239.
66. [31a] C. J. Marsden, J. Fluorine Chem. 1975, 5, 401-422.
67. [31b] D. A. Lone, Roman Spcctroscopy, Me Graw-Hill Int. Book Company, New York, 1977, p. 158.
68. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Client. Soc., Perkin Trans. 2 1987, S1-S17.
69. [30], chapter 3, pp. 82-86.
70. P. D'Antonio, C. George, A. H. Lowrey, J. Karle, J. Chem. Phys. 1971,55, 1071-1075.
71. J. J. BeiBruno, Heteroatom Cliem. 1996, 7, 39-43.
72. C. J. Marsden, G. M. Sheldrick, J. Mol. Struct. 1971, 10, 419-425.
73. G. D. Morris, F. W. B. Eintein, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1986, C42, 1433-1435.
74. T. G. Back, P. W. Codding, Can. J. Cliem. 1983,61, 2449-2751.
75. N. Bertel, H. W. Roesky, F. T. Edelmann, M. Noltemeyer, H. G. Schmidt, Z. Anorg. Allg. Client. 1990, 586, 7-18.
76. I. Waener, W. W. du Mont, S. Pohl, W. Saak, Client. Ber. 1990, 123, 2325-2327.
77. H. J. Emeléus, N. Welcman, J. Client. Soc. 1963, 1268-1271.
78. D. Christen, H. Oberhammer, W. Zeil, A. Haas, A. Darmadi, J. Mol. Struct. 1980, 66, 203-211.
79. J. S. Rutherford, C. Calvo, Z. Kristallogr. 1969, 128, 229.
80. E. R. Cullen, F. S. Guziec, Jr., C. J. Murphy, T. C. Wong, K. K. Anderson, J. Ant. Client. Soc. 1981, 103, 7055-7057.
81. H. E. Hallam, C. M. Jones, J. Mol. Struct. 1970, 5, 1-19.
82. [46a] R. S. Balestrero, D. M. Forkey, J. G. Rüssel, Magii. Reson. Client. 1986, 24, 651-655.
83. [46b] 1.1. Padilla-Martinez, N. Andrade-Löpez, M. Gama-Goicochea, E. Aguilar-Cruz, A. Cruz, R. Contreras, H. Tlahuext, Heteroatom Client. 1996, 7, 323-335.
84. An ab initio calculation for the tautomerism selenoformamid/ selenoformimidic acid is reported: J. Leszczynski, J. S. Kwiatkowski, D. Leszczynski, J. Am. Client. Soc. 1992, 114, 10089-10091.
85. [48a] H Kaeeyama, K. Kido, S. Kato, T. Murai, J. Client. Soc., Perkin Trans l 1994, 1083-1088.
86. [48b] S. Kato, T. Kawachi, K. Ibi, S. Nakaiida, K. Kawai, T. Kanda, T. Murai, H. Ishihara, Heteroatom Client. 1995, 6, 215-221.
87. H. Blau, Dissertation, Univ. Münster, 1994.
88. [50a] H Fische, K Treier, c. Troll, R. stumpf, J. Client. Soc., Client. Commun. 1995, 2461-2462.
89. [50b] H. Fischer, C. Kaibas, R. Stumpf, Client. Ber. 1996, 729, 1169-1175.
90. C. Piccini-Leopardi, O. Fahre, D. Zimmermann, J. Reisse, F. Cornea, C. Fulea, Org. Magn. Reson. 1976, 8, 536-538.
91. T. C. Wong, F. S. Guziec, Jr., C. Moustakis, J. Cltem. Soc., Perkin Traits. 2 1983, 1471-1475.
92. R. J. Abraham, S. L. R. Ellison, M. Barfield, W. A. Thomas, J. Client. Soc., Perkin Trans. 2 1987, 977-985.
93. P. R. Brooks, J. A. Counter, R. Bishop, E. R. T. Tiekink, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1991, C47, 1939-1941.
94. K. Okuma, K. Ojima, I. Kaneko, Y. Tsujimoto, H. Ohta, Y. Yokomori, J. Client. Soc., Perkin Trans, l 1994, 2551-2159.
95. J. Grobe, D. Le Van, H. Wiese, unpublished results.
96. [57a] A Marinetti, p. Mathey, J. Client. Soc., Client. Commun. 1990, 153-154.
97. [57bJ F. Mathey, Ace. Client. Res. 1992, 25, 90-96.
98. N. Welcman, H. Regev, J. Cliem. Soc. 1965, 7511-7514.
99. A. E. Finholt, A. C. Bond, K. E. Wilzbach, H. J. Schlesinger, J. Am. Client. Soc. 1947, 69, 2692-2696.
100. [60a] A. J. Hubert, H. G. Viehe, J. Client. Soc. C 1968, 228-230.
101. [60b] E. J. Corey, D. E. Cane, J. Org. Cliem. 1970, 35, 3405-3409.
102. Further details of the crystal structure investigations may be obtained from the Fachinformationszentrum Karlsruhe, D-76344 Eecenstein-Leopoldshafen (Germany), on quoting the depository numbers CSD-406305 (6c), -406306 (7b), -406307 (9a), and -406304 (13b) the names of the authors, and the journal citation.
103. G. M. Sheldrick, SHELXL-93, Program for Crystal Structure Determination, University of Göttingen, 1993.