Acid catalysis vs. electron-transfer catalysis via organic cations or cation-radicals as the reactive intermediate. Are these distinctive mechanisms?

Acta Chemica Scandinavica

Volumn 52, Issue 1, 1998, Pages 114-130

  Rathore, Rajendra ^a   Kochi, Jay K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001758806     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.52-0114     Document Type: Article

References (105)

1. (a) Kiselev, S. and Konovalov, S. Russ. Chem. Rev. 58 (1989) 230;
2. (b) Yates, P. and Eaton, P. J. Am. Chem. Soc. 82 (1960) 4436 and references therein;
3. (c) Fray, G. I. and Robinson, R. J. Am. Chem. Soc. 83 (1961) 249;
4. (d) Houk, K. N. and Strozier, R. W. J. Am. Chem. Soc. 95 (1973) 4095;
5. (e) Grieco, P. A., Nunes, J. J. and Gaul, M. D. J. Am. Chem. Soc. 112 (1990) 4595.
6. (a) Lutz, R. P. Chem. Rev. 84 (1984) 205;
7. (b) Breslow, R. and Hoffman, J. M., Jr. J. Am. Chem. Soc. 94 (1972) 2111;
8. (c) Dauben, W. G. and Chollet, A. Tetrahedron Lett. 22 (1981) 1583;
9. (d) Ziegler, F. E. Acc. Chem. Res. 10 (1977) 227.
10. (a) Scmitz, E. and Eichhorn, J. In: Patai, S., Ed., The Chemistry of Ether Linkage, Wiley, 1967;
11. (b) Fife, T. H. Acc. Chem. Res. 8 (1972) 264;
12. (c) Sterzycki, R. Synthesis (1979) 724;
13. (d) Cordes, E. H. and Bull, H. G. Chem. Rev. 74 (1974) 581;
14. (e) Shono, T. and Matsumura, Y. J. Am. Chem. Soc. 91 (1969) 2803.
15. (a) Parker, R. E. and Isaacs, N. S. Chem. Rev. 59 (1959) 737;
16. (b) Collins, C. J. Q. Rev. Chem. Soc. 14 (1960) 357 and references therein;
17. (c) Nakamura, E. and Kuwajima, I. J. Am. Chem Soc. 99 (1977) 961.
18. (a) Bartók, M. and Molnár, Á. In: Patai, S., Ed., The Chemistry of Functional Groups, Supplement E, Wiley, New York 1980, p. 722-733;
19. (b) Pocker, Y. and Ronald, B. P. J. Org. Chem. 35 (1970) 3362;
20. (c) Pocker, Y. and Ronald, B. P. J. Am. Chem. Soc. 92 (1970) 3385;
21. (d) Gebhardt, H. J. and Adams, K. H. J. Am. Chem. Soc. 76 (1954) 3925 and references therein.
22. (a) Fischer, P. In: Patai, S., Ed., The Chemistry of Functional Groups, Supplement E, Wiley, New York 1980, p. 761-820;
23. (b) Capon, B. 'Reaction of Aldehydes and Ketones and Their Derivatives', in Organic Reaction Mechanism, Wiley, London 1977.
24. Herling, J., Shabtai, J. and Gil-Av, E. J. Am. Chem. Soc. 87 (1985) 4107 and references therein.
25. (a) Yoshida, K. Electrooxidation in Organic Chemistry. The Role of Cation Radicals as Synthetic Intermediates, Wiley, New York 1984, p. 130ff;
26. (b) Bosch, E. and Kochi, J. K. J. Org. Chem. 59 (1994) 3314;
27. (c) White, E. H., DePinto, J. T., Polito, A. J., Bauer, I. and Roswell, D. F. J. Am. Chem. Soc. 110 (1988) 3708;
28. (d) Welch, C. M. and Smith, H. A. J. Am. Chem. Soc. 73 (1951) 4391.
29. (a) Banthorpe, D. V. Top. Carbocyc. Chem. 1 (1969) 1-62;
30. (b) Shine, H. J. and Stanley, J. P. J. Org. Chem. 32 (1967) 905;
31. (c) Hammond, G. S. and Clovis, J. S. J. Org. Chem. 28 (1963) 3283;
32. (d) Banthorpe, D. V. Chem. Rev. 70 (1970) 295.
33. (a) March, J. Advanced Organic Chemistry, 4th ed., Wiley, New York 1992;
34. (b) Larock, R. C. Comprehensive Organic Transformations, VCH, New York 1989, p. 628-633;
35. (c) Miyashita, N., Yoshikoshi, A. and Grieco, P. A. J. Org. Chem. 42 (1977) 3772 and references therein.
36. (a) Tashio, M. Synthesis (1979) 921;
37. (b) Wang, Z. Y., Berard, N., Wisniewska, I. and Hay, A. S. J. Org. Chem. 55 (1990) 4966;
38. (c) Rickborn, B. In: Trost, B. M., Ed., Comprehensive Organic Synthesis, Pergamon, Oxford 1991, Vol 3, p. 721 and references therein.
39. Huheey, J. E. Inorganic Chemistry: Principles of Structure and Reactivity, Harper and Row, New York 1973, p. 212.
40. Chanon, M. Bull. Soc. Chim. Fr (1985) 211.
41. Bauld, N. L. In: Mariano, P., Ed., Advances in ElectronTransfer Chemistry, JAI Press, London 1992, Vol. 2, pp. 1-66.
42. (a) Eberson, L. and Jönsson, L. J. Chem. Soc., Chem. Commun. (1980) 1187;
43. (b) Eberson, L., Jönsson, L. and Wistrand, L.-G. Tetrahedron 38 (1982) 1087.
44. Also see, (a) Alder, R. W. J. Chem. Soc., Chem. Commun. (1980) 1184; (b) Jönsson, L. and Wistrand, L.-G. J. Org. Chem. 49 (1984) 3340.
45. Also see, (a) Alder, R. W. J. Chem. Soc., Chem. Commun. (1980) 1184; (b) Jönsson, L. and Wistrand, L.-G. J. Org. Chem. 49 (1984) 3340.
46. (a) Bauld, N. L. Tetrahedron 50 (1994) 12685, and references therein;
47. (b) Malcoch, J. and Steckhan, E. Tetrahedron Lett. 28 (1987) 1081;
48. (c) Schmittel, M. and Wöhrle, C. J. Org. Chem. 60 (1995) 8223, and references therein.
49. (a) Lopez, L., Mele, G. and Mazzeo, C. J. Chem. Soc., Perkin Trans. 1 (1994) 779;
50. (b) Arce de Sanabia, J. and Carrión, A. E. Tetrahedron Lett. 34 (1993) 7837.
51. (a) Lopez, L. and Troisi, L. Tetrahedron Lett. 30 (1989) 3097;
52. (b) Lopez, L., Mele, G., Fiandanese, V., Candellicchio, C. and Nacci, A. Tetrahedron 50 (1994) 9097;
53. (c) Delavnay, J., Lebouc, A., Tallec, A. and Simonet, J. J. Chem. Soc., Chem. Commun. (1982) 387;
54. (d) Bosch, E. and Kochi, J. K. J. Am. Chem. Soc. 118 (1996) 1319.
55. (a) Nelsen, S. F. Acc. Chem. Res. 20 (1987) 269, and references therein;
56. (b) Kim, T., Mirafzal, G. A., Liu, J. and Bauld, N. L. J. Am. Chem. Soc. 115 (1993) 7653.
57. Dhanalekshmi, C. S. V. and Balasubramanian, K. K. J. Chem. Soc., Chem. Commun. (1994) 511, and references therein.
58. (a) Ledwith, A. Acc. Chem. Res. 5 (1972) 133;
59. (b) Prousek, J. Chem. Listy 89 (1995) 144;
60. (c) Cedheim, L. and Eberson, L. Acta Chem. Scand., Ser. B 30 (1976) 527;
61. (d) Bauld, N. L., Bellville, D. J., Harirchian, B., Lorenz, K. T., Pabon, R. A., Jr., Reynolds, D. W., Wirth, D. D., Chiou, H.-S. and Marsh, B. K. Acc. Chem. Res. 20 (1987) 371;
62. (e) Bookman, T. M., Kosynkin, D. and Kochi, J. K. J. Am. Chem. Soc. 119 (1997) 4846.
63. Hart, H., Teuerstein, A. and Babin, M. A. J. Am. Chem. Soc. 103 (1981) 903.
64. (a) Gassman, P. G. and Singleton, D. A. J. Am. Chem. Soc. 106 (1984) 7993;
65. (b) Yueh, W. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1995) 871.
66. (c) Ciminale, F., Lopez, L. and Mele, G. Tetrahedron 50 (1994) 12687.
67. (a) Eberson, L., Olofsson, B. and Svensson, J.-O. Acta Chem. Scand. 46 (1992) 1005;
68. (b) Kim, T., Sarker, H. and Bauld, N. L. J. Chem. Soc., Perkin Trans. 2 (1995) 577 and references therein;
69. (c) Han, D. S. and Shine, H. J. J. Org. Chem. 61 (1996) 3977;
70. (d) Uneyama, K., Isimura, A., Fujii, I. and Torii, S. Tetrahedron Lett. (1983) 2857, and references therein;
71. (e) Rathore, R. and Kochi, J. K. J. Org. Chem. 60 (1995) 7479.
72. (a) Kaiser, E. T. and Kevan, L. Radical Ions, Wiley, New York 1968;
73. (b) Forbes, W. F. and Sullivan, P. D. Can. J. Chem. 44 (1966) 1501;
74. (c) Nishinaga, A., Ziemek, P. and Matsura, T. J. Chem. Soc. C (1970) 2613;
75. (d) Sankararaman, S., Lau, W. and Kochi, J. K. J. Chem. Soc., Chem. Commun. (1991) 396.
76. (a) Eberson, L. and Radner, F. J. Chem. Soc. Chem. Commun. (1991) 1233;
77. (b) Eberson, L. and Radner, F. Acta Chem. Scand. 45 (1991) 1093, and references therein;
78. (c) Davies, A. G. Chem. Soc. Rev. 25 (1996) 299 and references therein;
79. (d) Also see Hart et al. in Ref. 23.
80. (a) Eberson, L. and Radner, F. Acta Chem. Scand. 46 (1992);
81. (b) Valenzuela, J. A. and Bard, A. J. J. Phys. Chem. 72 (1968) 286;
82. (c) Also see Kaiser et al. in Ref. 26a.
83. -1 (see the Experimental section).
84. (a) See Hart, H. et al. in Ref. 23;
85. (b) Kim, E. K. and Kochi, J. K. J. Am. Chem. Soc. 113 (1991) 4462.
86. (a) Al-Ekabi, H., Kawata, H. and de Mayo, P. J. Org. Chem. 53 (1988) 1471;
87. (b) Azarani, A., Berinstain, A. B., Johnston, L. J. and Kazanis, S. J. Photochem. Photobiol. A: Chem. 57 (1991) 175, and references therein.
88. Svanholm, U., Jensen, B. S. and Parker, V. D. J. Chem. Soc., Perkin Trans. 2 (1974) 907.
89. Rathore, R. and Kochi J. K. J. Org. Chem. 60 (1995) 4399.
90. 2 and estimation of the energetics of eqn. (7).
91. However, the presence of the quinone oxidant ensures that the equilibrium is pulled to completion; see Handoo, K. L. and Gadru, K. Curr. Sci. 55 (1986) 920.
92. See Hammerich, O. and Parker, V. D. Acta Chem. Scand., Ser. B 36 (1982) 63.
93. See: Freedman, H. H. In: Olah, G. A. and Schleyer, P. V. R., Eds., Carbonium Ions, Vol IV, Wiley, New York 1973, p. 1501ff.
94. See: Hubig, S. M., Jung, W. and Kochi, J. K. J. Org. Chem. 59 (1994) 6233.
95. 1/2=0.89 V vs. SCE in dichloromethane; Weigand, U. Unpublished results.
96. + (E°=1.50 V) effects the benzylic coupling to high yields to establish the efficacy of electron-transfer catalysis.
97. Rathore, R., Bosch, E. and Kochi, J. K. Tetrahedron Lett. 50 (1994) 6727.
98. Suter, C. M. and Maxwell, C. E. Org. Synth., Coll. Vol. 2 (1943) 485.
99. Rathore, R., Weigand, U. and Kochi, J. K. J. Org. Chem. 61 (1996) 5246.
100. Bruson, H. A. and Kroeger, J. W. J. Am. Chem. Soc. 62 (1940) 36.
101. Fieser, L. F. and Fieser, M. Reagents for Organic Synthesis 1 (1967) 136.
102. Perrier, S., Sankararaman, S. and Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 (1993) 825.
103. Singh, P. and Rangaswami, S. Tetrahedron Lett. (1966) 1229.
104. Hunt, S. E. and Lindsey, A. S. J. Chem. Soc. (1962) 4550.
105. Gill, G. B. and Hands, D. Tetrahedron Lett. (1971) 181.