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22. Radical anions and cations derived from CDC, CDO or CDN groups 1351

70.R. J. Robbins and D. E. Falvey, J. Org. Chem., 58, 3616 (1993).

71.D.-Y. Yang and T. P. Begley, Tetrahedron Lett., 34, 1709 (1993).

72.T. Shono, S. Kashimura, Y. Mori, T. Hayashi, T. Soejima and Y. Yamaguchi, J. Org. Chem., 54, 6001 (1989).

73.T. Shono, Y. Morishima, N. Moriyoshi, M. Ishifune and S. Kashimura, J. Org. Chem., 59, 273 (1994).

74.J. M. Aurrecoechea and M. Solay, Tetrahedron Lett., 36, 2501 (1995).

75.For additional examples of ketone/olefin coupling reactions promoted by Sml2, see:

(a)S. Fukazawa, A. Nakanishi, T. Fujinami and S. Sakai, J. Chem. Soc., Perkin Trans. 1, 1669 (1988).

(b)M. Kawatsura, F. Matsuda and H. Shirahama, J. Org. Chem., 59, 6900 (1994).

76.D. Griller and K. U. Ingold, Acc. Chem. Res., 13, 317 (1980).

77.D. P. Curran, in Advances in Free Radical Chemistry, Vol. 1 (Ed. D. D. Tanner), JAI Press, Greenwich, CT, 1990, pp. 121 157.

78.D. Belotti, J. P. Pete and C. Portella, J. Org. Chem., 51, 4196 (1986).

79.Reductive cyclizations were reported by Shono as early as 1971. The success of the reaction is highly dependent on the nature of the cathodic material. Carbon rod has been found to give both high yields and diastereoselectivities. See T. Shono and M. Mitani, J. Am. Chem. Soc., 93, 5284 (1971); T. Shono, I. Nishiguchi, H. Ohmizu, and M. Mitani, J. Am. Chem. Soc., 100, 545 (1978).

80.J. E. Swartz, T. J. Mahachi and E. Kariv-Miller, J. Am. Chem. Soc., 110, 3622 (1988).

81.For an example involving the use of DMPC at a lead cathode, see P. B. Lawlin, A. C. Hutson and E. Kariv-Miller, J. Org. Chem., 54, 526 (1989).

82.T. Shono, H. Masuda, H. Murase, M. Shimomura and S. Kashimura, J. Org. Chem., 57, 1061 (1992).

83.E. Kariv-Miller, H. Maeda and F. Lombardo, J. Org. Chem., 54, 4022 (1989).

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102.(a) S. Fukuzawa, A. Nakanishi, T. Fujinami and S. Sakai, J. Chem. Soc., Perkin Trans. 1, 1669 (1988).

(b) M. Kawatsura, F. Matsuda and H. Shirahama, J. Org. Chem., 59, 6900 (1994).

103.G. H. Lee, E. B. Choi, E. Lee and S. P. Chwang, J. Org. Chem., 59, 1428 (1994).

104. Aminium and other cation radical salts may be synthesized by a procedure given in

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105.See, for example:

ˇ

(a) J. Gunic,´ I. Tabakovic´ and Z. Sanickanin,ˇ Electrochim. Acta, 35, 225 (1990).

1352

Daniel J. Berger and James M. Tanko

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107.See, for example, A. Gieseler, E. Steckhan, O. Wiest and F. Knoch, J. Org. Chem., 56, 1405 (1991).

108.W. P. Todd, J. P. Dinnocenzo, S. Farid, J. L. Goodman and I. R. Gould, J. Am. Chem. Soc., 113, 3601 (1991).

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D. D. Wirth, H.-S. Chiou and B. K. Marsh, Acc. Chem. Res., 20, 371 (1987).

111.N. L. Bauld, Tetrahedron, 45, 5307 (1989).

112.N. L. Bauld, Adv. Electron Transfer Chem., 2, 1 (1992).

113.P. G. Gassman and D. A. Singleton, J. Am. Chem. Soc., 106, 6085, 7993 (1984).

114.(a) Reference 106a.

(b) L. Eberson and B. Olofsson, Acta Chem. Scand., 42, 336 (1988). See also References 110, 111 and 112.

115.(a) W. Yueh and N. L. Bauld, J. Chem. Soc., Perkin Trans. 2, 871 (1995).

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(b) Y. Inoue, T. Okano, N. Yamasaki and A. Tai, J. Photochem. Photobiol. A., 66, 61 (1992). See also References 110, 111 and 112.

119.K. Chockalingam, M. Pinto and N. L. Bauld, J. Am. Chem. Soc., 112, 447 (1990).

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121.S. E. Nigenda, D. M. Schleich, S. C. Narang and T. Keumi, J. Electrochem. Soc., 134, 2465 (1987).

122.J. Mlcoch and E. Steckhan, Tetrahedron Lett., 28, 1081 (1987).

123.J. Mattay, G. Trampe and J. Runsink, Chem. Ber., 121, 1991 (1988).

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132.J. P. Dinnocenzo and D. A. Conlon, J. Am. Chem. Soc., 110, 2324 (1988).

133.See, for example, J. P. Dinnocenzo and M. Schmittel, J. Am. Chem. Soc., 109, 1561 (1987).

134.H. Weng, V. Sethuraman and H. D. Roth, J. Am. Chem. Soc., 116, 7021 (1994).

135.N. L. Bauld and G. A. Mirafzal, J. Am. Chem. Soc., 113, 3613 (1991).

136.V. Ullrich, Top. Curr. Chem., 83, 67 (1979).

137.J. T. Groves and T. E. Nemo, J. Am. Chem. Soc., 105, 5786, 5791 (1983).

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22. Radical anions and cations derived from CDC, CDO or CDN groups 1353

139.(a) A. J. Castellino and T. C. Bruice, J. Am. Chem. Soc., 110, 1313 (1988).

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140.See J. T. Groves and Y. Watanabe, J. Am. Chem. Soc., 108, 507 (1986).

141.J. T. Groves and M. K. Stern, J. Am. Chem. Soc., 109, 3812 (1987).

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143.A. J. Castellino and T. C. Bruice, J. Am. Chem. Soc., 110, 7512 (1988).

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149.G. A. Mirafzal and N. L. Bauld, J. Am. Chem. Soc., 114, 5457 (1992).

150.G. A. Mirafzal, J. Liu and N. L. Bauld, J. Am. Chem. Soc., 115, 6072 (1993).

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´

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