Preparation and Structures of Crystalline Aromatic Cation-Radical Salts. Triethyloxonium Hexachloroantimonate as a Novel (One-Electron) Oxidant

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5847-5856

  Rathore, R ^a   Kumar, A S ^a   Lindeman, S V ^a   Kochi, J K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001148576     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980407a     Document Type: Article

References (84)

1. (a) Hart, H.; Teuerstein, A.; Babin, M. A. J. Am. Chem. Soc. 1981, 103, 903.
2. (b) Bhattacharya, A.; DiMichele, L. M.; Dolling, U.-H.; Grabowski, E. J. J.; Grenda, V. J. J. Org. Chem. 1989, 54, 6118.
3. (c) Andersen, M. L.; Handoo, K. L.; Parker, V. D. Acta Chem. Scand. 1991, 45, 983.
4. (d) Bauld, N. L.; Bellville, D. J.; Harirchian, B.; Lorenz, K. T.; Pabon, P. A., Jr.; Reynolds, D. W.; Wirth, D. D.; Chiou, H. S.; Marsh, B. K. Acc. Chem. Res. 1987, 20, 371.
5. (e) Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3864.
6. (a) Chanon, M. Bull. Soc. Chim. Fr. 1985, 209.
7. (b) Eberson, L. Electron-Transfer Reactions in Organic Chemistry; Springer: New York, 1987.
8. (c) Dinnocenzo, J. P.; Banach, T. E. J. Am. Chem. Soc. 1986, 108, 6063.
9. (d) Richardson, T. J.; Bartlett, N. J. Chem. Soc., Chem. Commun. 1974, 427.
10. (e) Snider, B. B.; Kwon, T. J. Org. Chem. 1990, 55, 4786.
11. (f) Panday, G. Top. Curr. Chem. 1993, 168, 175.
12. (a) Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
13. (b) McClend, C. W. In Synthetic Reagents; Pizey, J. S., Ed.; Wiley: New York, 1983; p 85.
14. (c) Uemura, S. In Synthetic Reagents; Pizey, J. S., Ed.; Wiley: New York, 1983; p 165.
15. (d) Bock, H.; Brähler, G.; Henkel, U.; Schleker, R.; Seebach, D. Chem. Ber. 1980, 113, 289.
16. (e) Mijs, W. J.; deJonge, C. R. H. I. Organic Synthesis by Oxidation by Metal Complexes; Plenum: New York, 1986.
17. (a) Chanon, M.; Fox, M.-A. Photoinduced Electron Transfer, Parts A-D; Elsevier: Amsterdam, 1988.
18. (b) Roth, H. D. Top. Curr. Chem. 1992, 163, 131.
19. (c) Mattay, J. Synthesis 1989, 233.
20. (d) Yoshida, K. Electrooxidation in Organic Chemistry. The Role of Cation Radicals as Synthetic Intermediates; Wiley: New York, 1984.
21. (e) Kyriacou, D. Modern Electroorganic Chemistry; Springer: Berlin, 1994.
22. (f) Also see: Fry, A. J. Synthetic Organic Electrochemistry; Wiley: New York, 1989.
23. (a) Brandys, M.; Sassoon, R. E.; Rabani, J. J. Phys. Chem. 1987, 91, 953.
24. (b) O'Neill, P.; Steenken, S.; Schulte-Frohlinde, D. J. Phys. Chem. 1975, 79, 2773.
25. (c) For a review see: Baxendale, J. H.; Rodgers, M. A. J. Chem. Soc. Rev. 1978, 7, 235 and references therein.
26. (a) Enkelmann, V. Synth. Met. 1991, 42, 2547.
27. (b) Yoshizawa, K.; Chano, A.; Ito, A.; Tanaka, K.; Yamabe, T.; Yamauchi, J.; Shiro, M. J. Am. Chem. Soc. 1992, 114, 5994.
28. (c) Rathore, R.; Lindeman, S. V.; Kochi, J. K. Angew. Chem. Int. Ed. 1998, 37, 1585.
29. (a) Law, K. Y. Chem. Rev. 1993, 93, 449.
30. (b) Baumgarten, M.; Müllen, K. Top. Curr. Chem. 1994, 169, 1.
31. Determined by searching through the Cambridge Crystallography Data Base (Release Fall 1997).
32. With strong electrophilic properties and prone to rapid proton loss, fragmentation, etc. See: (a) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550. (b) Albini, A.; Fasani, E.; Dalessandro, N. Coord. Chem. Rev. 1993, 125, 269.
33. With strong electrophilic properties and prone to rapid proton loss, fragmentation, etc. See: (a) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2550. (b) Albini, A.; Fasani, E.; Dalessandro, N. Coord. Chem. Rev. 1993, 125, 269.
34. (a) Musker, W. K.; Woldford, T. L. J. Am. Chem. Soc. 1976, 98, 3055.
35. (b) Also see: Bandlish, B. K.; Shine, H. J. J. Org. Chem. 1977, 42, 561.
36. (a) Bell, F. A.; Ledwith, A.; Sherrington, D. C. J. Chem. Soc. C 1969, 13, 2719.
37. (b) Luken, E. A. C. J. Chem. Soc. 1969, 4963.
38. (c) Cowell, G. W.; Ledwith, A.; White, A. C.; Woods, H. J. J. Chem. Soc. B 1970, 227.
39. - + NO.
40. Kim, E. K.; Kochi, J. K. J. Am. Chem. Soc. 1991, 113, 4962.
41. (a) Meerwein, H.; Battenberg, E., Gold, H.; Pfeil, E.; Willfang, G. J. Prakt. Chem. 1939, 154, 83.
42. (b) Previous indications that triethyloxonium hexachloroantimonate can be involved in other than ethylation reactions were reported by Böttger, G.; Geisler, A.; Fröhlich, R.; Wüthwein, E.-U. J. Org. Chem. 1997, 62, 6407 and references therein.
43. (a) Rathore, R.; Kochi, J. K. J. Org. Chem. 1995, 60, 4399.
44. (b) Rathore, R.; Kochi, J. K. Acta Chem. Scand. 1998, 52, 114.
45. (c) Tanaka, F.; Mataga, N. Bull. Chem. Soc. Jpn. 1973, 46, 1591.
46. (a) The reduced antimony(III) trichloride moiety has been crystallographically identified as a (polymeric) chloride complex.
47. (b) Rathore, R.; Lindeman, S. V.; Kumar, A. S.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6931-6939.
48. Smith, J. R. L.; McKeer, L. C.; Tayler, J. M. J. Chem. Soc., Perkin Trans. 2 1988, 385.
49. (a) Kovacic, P.; Sparks, A. K. J. Am. Chem. Soc. 1960, 82, 5740.
50. (b) Kovacic, P. In Friedel Crafts and Related Reactions, Vol. IV; Olah, G. A., Ed.; Interscience: New York, 1965.
51. (c) Rathore, R.; Loyd, S. H.; Kochi, J. K. J. Am. Chem. Soc. 1994, 116, 8414.
52. (a) Nugent, W. A. J. Org. Chem. 1980, 45, 4533.
53. (b) Shouji, E.; Yamamoto, K.; Tsuchida, E. Chem. Lett. 1993, 1927.
54. (c) Mori, T.; Rathore, R.; Lindeman, S. V.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1998, 927.
55. -1.
56. Radner, F. Acta Chem. Scand. 1989, 43, 481.
57. Rathore, R.; Lindeman, S. V.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 9393.
58. Meerwein, H.; Hinz, G., Hoffman, P.; Kroning, E.; Pfeil, E. J. Prakt. Chem. 1937, 147, 257. Also see: Perst, H. In Carbonium Ions; Olah, G. A., Schleyer, P., Eds.; Wiley: New York, 1976; Vol. 3, pp 1961 ff.
59. Meerwein, H.; Hinz, G., Hoffman, P.; Kroning, E.; Pfeil, E. J. Prakt. Chem. 1937, 147, 257. Also see: Perst, H. In Carbonium Ions; Olah, G. A., Schleyer, P., Eds.; Wiley: New York, 1976; Vol. 3, pp 1961 ff.
60. -1.
61. -], as described by Meerwein et al. in ref 14.
62. Compare: Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley: New York, 1988; p 395.
63. -).
64. As speculatively discussed by Kovacic and co-workers in ref 18a.
65. Compare: (a) Kobayashi, T.; Kubota, T.; Ezumi, K. J. Am. Chem. Soc. 1983, 105, 2172. (b) Nakazawa, T.; Murata, I. J. Am. Chem. Soc. 1977, 99, 1996. (c) Inagaki, S.; Yamamura, K.; Nakasugi, K.; Nakazawa, T.; Murata, I. J. Am. Chem. Soc. 1981, 103, 2093.
66. Compare: (a) Kobayashi, T.; Kubota, T.; Ezumi, K. J. Am. Chem. Soc. 1983, 105, 2172. (b) Nakazawa, T.; Murata, I. J. Am. Chem. Soc. 1977, 99, 1996. (c) Inagaki, S.; Yamamura, K.; Nakasugi, K.; Nakazawa, T.; Murata, I. J. Am. Chem. Soc. 1981, 103, 2093.
67. Compare: (a) Kobayashi, T.; Kubota, T.; Ezumi, K. J. Am. Chem. Soc. 1983, 105, 2172. (b) Nakazawa, T.; Murata, I. J. Am. Chem. Soc. 1977, 99, 1996. (c) Inagaki, S.; Yamamura, K.; Nakasugi, K.; Nakazawa, T.; Murata, I. J. Am. Chem. Soc. 1981, 103, 2093.
68. See: Rathore et al. in ref 15a.
69. Kunzenhofer, K.; de Boer, J. J. Z. Kristallogr. 1970, 131, 103.
70. Badger, B.; Brocklehurst, B. Trans. Faraday Soc. 1969, 65, 2582, 2588.
71. Takahashi, S.; Sankararaman, S.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 2954.
72. See: Jones, J. B.; Brown, D. S.; Hales, K. A.; Massey, A. G. Acta Crystallogr. 1988, C44, 1757 for the structure of neutral donor.
73. Compare the molecular structure of other cationic π-dimers. (a) Kröhnke, C.; Enkelmann, V.; Wegner, G. Angew. Chem., Int. Ed. Engl. 1980, 19, 912. (b) Lau, W.; Kochi, J. K. J. Org. Chem. 1986, 51, 1801.
74. Compare the molecular structure of other cationic π-dimers. (a) Kröhnke, C.; Enkelmann, V.; Wegner, G. Angew. Chem., Int. Ed. Engl. 1980, 19, 912. (b) Lau, W.; Kochi, J. K. J. Org. Chem. 1986, 51, 1801.
75. Wright, J. D. Molecular Crystals; Cambridge: New York, 1987; p 155 ff.
76. Rathore, R.; Bosch, E.; Kochi, J. K. Tetrahedron 1994, 50, 6727.
77. Rathore, R.; Weigand, U.; Kochi, J. K. J. Org. Chem. 1996, 61, 5246.
78. Welch, C. M.; Smith, H. A. J. Am. Chem. Soc. 1951, 73, 4391.
79. Bosch, E.; Kochi, J. K. J. Am. Chem. Soc. 1996, 118, 1319.
80. Suter, C. M.; Maxwell, C. E. Org. Synth. Coll. Vol. 2 1943, 485.
81. Pentamethylphenylpropanoyl chloride was prepared according to a slightly modified literature procedure (Gasparini, G. M. Gazz. Chim. Ital. 1979, 109, 357). Further details will be published elsewhere.
82. Jaxa-Chamiec, A.; Shah, V. P.; Kruse, L. I. J. Chem. Soc., Perkin Trans. 1 1989, 1705.
83. Sheldrick, G. M. SHELSX-86, Program for Structure Solution; University of Göttingen: Germany, 1986.
84. (a) Note that the reported structure of triethyloxonium cation is heavily disordered. See: Watkins, M. I.; Ip, W. M.; Olah, G. A.; Ban, R. J. Am. Chem. Soc. 1982, 104, 2365 and also see Experimental Section.