Patai S., Rappoport Z. 1996 The chemistry of functional groups. The chemistry of amino, nitroso, nitro and related groups / 0379 422

65.A. Bencini, A. Bianchi, E. Garcia-Espana,˜ M. Giusti, S. Mangani, M. Micheloni, P. Orioli and P. Paoletti, Inorg. Chem., 26, 1243 (1987).

66.A. Bencini, A. Bianchi, E. Garcia-Espana,˜ M. Micheloni and P. Paoletti, Inorg. Chem., 27, 176 (1988).

67.B. Dietrich, M. W. Hosseini, J. -M. Lehn and R. B. Sessions, Helv. Chim. Acta, 66, 1262 (1983).

68.M. Kodama, E. Kimura and S. Yamaguchi, J. Chem. Soc. Dalton Trans., 2536 (1980).

69.G. Bojensen, J. Am. Chem. Soc., 109, 5557 (1987).

70.S. A. McLuckey, D. Cameron and R. G. Cooks, J. Am. Chem. Soc., 103, 1313 (1981).

71.G. S. Gorman, J. P. Speir, C. A. Turner and I. J. Amster, J. Am. Chem. Soc., 114, 3986 (1992).

72.G. Bojensen and T. Breindhal, J. Chem. Soc. Perkin Trans. 2, 1029 (1994).

73.Y. K. Lau, K. Nishizawa, R. Tse, A. S. Brown and P. Kebarle, J. Am. Chem. Soc., 103, 6291

(1981).

74. J. Oszczapowicz, in The Chemistry of Amidines and Related Compounds (Eds. S. Patai and

Z.Rappoport), Wiley, Chichester, 1991, pp. 623 688.

ˇ

75.J. Sevcikˇ and F. Grambal, in The Chemistry of Amidines and Imidates (Ed. S. Patai), Wiley, London, 1975.

76.J. Oszczapowicz and M. Kuminska,´ J. Chem. Soc., Perkin Trans. 2, 103 (1994).

77.A. Echavarren, A. Galan,´ J. -M. Lehn and J. de Mendoza, J. Am. Chem. Soc., 111, 4994 (1989).

78.A. Gleich, F. P. Schmidtchen, P. Mikulcik and G. Muller,¨ J. Chem. Soc., Chem. Commun., 55 (1990).

79.R. Schwesinger, Chimia, 39, 269 (1985).

80.(a) R. Schwesinger and H. Schlemper, Angew. Chem., Int. Ed. Engl., 26, 1167 (1987).

(b) R. Schwesinger, Nachr. Chem. Tec. Lab., 38, 1214 (1990).

81.M. H. Abraham, P. L. Grellier, D. V. Prior, J. J. Morris and P. J. Taylor, J. Chem. Soc., Perkin Trans. 2, 521 (1990).

82.E. D. Raczynska,´ C. Laurence and M. Berthelot, Can. J. Chem., 70, 2203 (1992).

83.J. -Y. Le Questel, C. Laurence, A. Lachkar, M. Helbert and M. Berthelot, J. Chem. Soc. Perkin Trans. 2, 2091 (1992).

84.A. Chardin, M. Berthelot, C. Laurence and D. G. Morris, J. Phys. Org. Chem., 7, 705 (1994).

85.D. B. Collum, Acc. Chem. Res., 26, 227 (1993).

86.(a) B. L. Lucht and D. B. Collum, J. Am. Chem. Soc., 116, 7949 (1994).

(b) A. S. Galianoroth, Y. J. Kim, J. H. Gilchrist, A. T. Harrison, D. J. Fuller and D. B. Collum,

J.Am. Chem. Soc., 113, 5053 (1991).

87.K. Bergander, R. X. He, N. Chandrakumar, O. Eppers and H. Gunther, Tetrahedron, 50, 5861 (1994).

88.J. Barluenga, R. Gonzalez, F. J. Fananas, M. Yus and F. Foubelo, J. Chem. Soc., Perkin Trans. 1, 1069 (1994).

89.F. E. Romesberg, J. H. Gilchrist, A. T. Harrison, D. J. Fuller and D. B. Collum, J. Am. Chem. Soc., 113, 5751 (1991).

90.W. Clegg, K. W. Henderson, R. E. Mulvey and P. A. Oneil, J. Chem. Soc., Chem. Commun., 769 (1994).

91.(a) B. L. Lucht and D. B. Collum, J. Am. Chem. Soc., 116, 6009 (1994),

(b) G. Becker, K. Hubler and J. Weidlein, Z. Anorg. Allgem. Chem., 620, 16 (1994),

(c) M. A. Nichols, D. Waldmuller and P. G. Williard, J. Am. Chem. Soc., 116, 1153 (1994),

(d) P. Kosse, E. Popowski, M. Veith and V. Huch, Chem. Ber., 127, 2103 (1994),

(e) F. E. Romesberg, M. P. Bernstein, J. H. Gilchrist, A. T. Harrison, D. J. Fuller and

D.B. Collum, J. Am. Chem. Soc., 115, 3475 (1993),

(f) B. Tecklenburg, U. Klingebiel and D. Schmidtbase, J. Organomet. Chem., 426, 287 (1992).

92.D. R. Armstrong, F. A. Banbury, I. Cragghine, M. G. Davidson, F. S. Mair, E. Pohl, P. R. Raithby and R. Snaith, Angew. Chem., Int. Ed. Engl., 32, 1769 (1993).

93.D. Sato, H. Kawasaki, I. Shimada, Y. Arata, K. Okamura, T. Date and K. Koga, J. Am. Chem. Soc., 114, 761 (1992).

94.M. P. Bernstein and D. B. Collum, J. Am. Chem. Soc., 115, 789 (1993).

95.N. P. Lorenzen, J. Kopf, F. Olbrich, U. Schumann and E. Weiss, Angew. Chem., Int. Ed. Engl., 29, 1441 (1990).

96.I. Cragghine, M. G. Davidson, O. Kocian, F. S. Mair, E. Pohl, P. R. Raithby, R. Snaith, N. Spencer and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 32, 1182 (1993).

97.F. E. Romesberg and D. B. Collum, J. Am. Chem. Soc., 116, 9187 (1994).

98.N. S. Nudelman, E. Lewkowicz and J. J. P. Furlong, J. Org. Chem., 58, 1847 (1993).

99.G. Boche, I. Langlotz, M. Marsch, K. Harms and N. E. S. Nudelman, Angew. Chem., Int. Ed. Engl., 31, 1205 (1992).

100.G. Boche, I. Langlotz, M. Marsch, K. Harms and G. Frenking, Angew. Chem., Int. Ed. Engl., 32, 1171 (1993).

101.A. Bencini, A. Bianchi, P. Dapporto, E. Garcia-Espana, M. Micheloni, P. Paoletti and P. Paoli,

J. Chem. Soc., Chem. Commun., 19, 1382 (1990).

102.E. M. Arnett, M. A. Nichols and A. T. McPhail, J. Am. Chem. Soc., 112, 7059 (1990).

103.C. Lambert, F. Hampel and P. Von R. Schleyer, Angew. Chem., Int. Ed. Engl., 31, 1209 (1992).

104.S. Bradamante, A. Marchesini and G. Pagani, J. Chem. Soc., Perkin Trans. 2, 568 (1973).

105.S. Bradamante and G. A. Pagani, J. Chem. Soc., Perkin Trans. 2, 1055 (1986).

106.E. Barchiesi and S. Bradamante, J. Phys. Org. Chem., 3, 139 (1990).

107.C. Gatti, A. Ponti, A. Gamba and G. Pagani, J. Am. Chem. Soc., 114, 8634 (1992).

108.E. Anders, A. Opitz and R. Boese, Chem. Ber., 125, 1267 (1992).

109.(a) A. Abbotto, S. Bradamante and G. A. Pagani, J. Org. Chem., 58, 444 (1993),

(b) S. Bradamante and G. A. Pagani, Pure Appl. Chem., 61, 709 (1989).

110.A. Abbotto, V. Alanzo, S. Bradamante and G. A. Pagani, J. Chem. Soc., Perkin Trans. 2, 481 (1991).

111.A. Abbotto, S. Bradamante and G. A. Pagani, J. Org. Chem.

112.E. Barchiesi, S. Bradamante, C. Carfagna and R. Ferraccioli, J. Chem. Soc., Perkin Trans. 2, 1565 (1988).

113.(a) A. J. Streitwieser, J. H. Hammons, E. Ciuffarin and J. I. Brauman, J. Am. Chem. Soc., 89, 59 (1967),

(b) A. J. Streitwieser, E. Ciuffarin and J. H. Hammons, J. Am. Chem. Soc., 89, 63 (1967),

(c) A. J. Streitwieser, E. Juaristi and L. L. Nebenzhal, in Comprehensive Carbanion Chemistry (Eds E. Buncel and T. Durst), Elsevier, Amsterdam, 1980.

114.E. S. Petrov, M. I. Terekhova and A. I. Shatenshtein, Zh. Obshch. Khim., 44, 1118 (1974).

115. W. S. Matthews, J. E. Bares, J. E. Bartmess, F. G. Bordwell, F. J. Cornforth, G. E. Drucker, Z. Margolin, R. J. McCallum, G. J. McCollum and N. R. Vanier, J. Am. Chem. Soc., 97, 7006 (1975).

116.R. R. Fraser, M. Bresse and T. S. Mansour, J. Chem. Soc., Chem. Commun., 620 (1983).

117.A. Streitwieser Jr, D. A. Bors and M. J. Kaufman, J. Chem. Soc. Chem. Commun., 1394 (1983).

118.D. A. Bors, M. J. Kaufman and A. J. Streitwieser, J. Am. Chem. Soc., 107, 6975 (1985).

119.S. Gronert and A. J. Streitwieser, J. Am. Chem. Soc., 108, 7016 (1986).

120.J. A. Krom, J. T. Petty and A. J. Streitwieser, J. Am. Chem. Soc., 115, 8024 (1993).

121.R. R. Fraser and T. S. Mansour, J. Org. Chem., 49, 3442 (1984).

122.W. K. McEwen J. Am. Chem. Soc., 58, 1124 (1936).

123.R. A. Cox, R. J. Stewart, J. Am. Chem. Soc., 98, 488 (1976).

124.(a) T. Birkall, W. L. Jolly, J. Am. Chem. Soc., 88, 5439 (1966),

(b)L. L. Lagowski, Pure Appl. Chem., 25, 429 (1971).

125.E. M. Arnett, T. C. Moriarty, L. E. Small, J. P. Rudolph and R. P. Quirk, J. Am. Chem. Soc., 95, 1492 (1973).

126.J. Courtot-Coupez and M. LeDemenez, Bull. Soc. Chim. Fr., 1033 (1969).

127.F. G. Bordwell and D. J. Algrim, J. Am. Chem. Soc., 110, 2964 (1988).

128.L. Grefenstein and G. Pagani, J. Org. Chem., 46, 3336 (1981).

129.F. G. Bordwell and M. J. Bausch, J. Am. Chem. Soc., 108, 2473 (1986).

130.I. E. Friedrich, J. Org. Chem., 48, 3851 (1983).

131.X. -M. Zhang and F. G. Bordwell, J. Am. Chem. Soc., 116, 904 (1994).

132.F. G. Bordwell and X. -M. Zhang, J. Am. Chem. Soc., 116, 973 (1994).

133.F. G. Bordwell, J. -P. Cheng, G. -Z. J. Ji, A. V. Satish and X. Zhang, J. Am. Chem. Soc., 113, 9790 (1991).

134.D. F. McMillen and D. M. Golden, Ann. Rev. Phys. Chem. 33, 493 (1982).

135.V. T. Varlamov and E. T. Denisov, Dokl. Akad. Nauk USSR, 293, 126 (1987).

136.J. H. Richardson, L. M. Stephenson and J. I. Brauman, J. Am. Chem. Soc., 97, 1160 (1975).

137.F. G. Bordwell, and T. -Y. Lynch, J. Am. Chem. Soc., 111, 7558 (1989).

138.(a) H. G. Viehe, Z. Janousek, R. Merenyi and L. Stella, Angew. Chem., Int. Ed. Engl., 18, 917 (1979),

(b)H. G. Viehe, Z. Janousek, R. Merenyi and L. Stella, Acc. Chem. Res., 18, 148 (1985).

139.F. G. Bordwell, J. P. Cheng, S. E. Seyedrezai and C. A. Wilson, J. Am. Chem. Soc., 110, 8178 (1988).

140.F. G. Bordwell, H. E. Fried, D. L. Hughes, T. -Y. Lynch, A. V. Satish and Y. E. Whang, J. Am. Chem. Soc., 55, 3330 (1990).

141.F. G. Bordwell, J. A. Harrelson and T. -Y. Lynch, J. Org. Chem., 55, 3337 (1990).

142.K. B. Wiberg and K. E. Laidig, J. Am. Chem. Soc., 109, 5935 (1987).

143.F. G. Bordwell and G. -Z. Ji, J. Am. Chem. Soc., 113, 8398 (1991).

144.F. G. Bordwell and G. -Z. Ji, J. Org. Chem., 57, 3019 (1992).

145.T. J. Hannigan and W. J. Spillane, J. Chem. Soc., Perkin Trans. 2, 851 (1982).

146.B. Unterhalt and E. Seebach, Arch. Pharm., 314, 51 (1981).

147.S. D. McDermott, P. O. Burke and W. J. Spillane, J. Chem. Soc., Perkin Trans. 2, 499 (1984).

148.P. O. Burke, S. D. McDermott, T. J. Hannigan and W. J. Spillane, J. Chem. Soc., Perkin Trans. 2, 1851 (1984).

149.L. Bauer and O. Exner, Angew. Chem., Int. Ed. Engl., 13, 376 (1974).

150.(a) J. Buglass, K. Hudson and J. G. Tillett, J. Chem. Soc. (B), 123 (1971),

(b)F. Di Furia, G. Modena and P. Scrimin, Nouv. J. Chim., 8, 45 (1984).

151.(a) M. Novak, G. A. Bonham, L. K. Molher and K. M. Peet, J. Org. Chem., 53, 3903 (1988),

(b)K. K. Ghosh, S. K. Rajput and K. K. Krishnani, J. Phys. Org. Chem., 5, 39 (1992).

152.(a) R. Pande and S. G. Tandom, Talanta, 38, 1015 (1991).

(b)M. Paul and R. Pande, Fresenius Z. Anal. Chem., 342, 193 (1992).

153.A. Bagno, C. Comuzzi and G. Scorrano, J. Am. Chem. Soc., 116, 916 (1994).

154.M. Decouzon, O. Exner, J. -F. Gal and P. -C. Maria, J. Org. Chem., 57, 1621 (1992).

155.E. Farkas and T. Kiss, J. Chem. Soc., Perkin Trans. 2, 1255 (1990).

156.E. Lipczynnska-Kochany and H. Iwamura, J. Org. Chem., 47, 5277 (1982).

157.(a) R. E. Plapinger, J. Org. Chem., 24, 802 (1959).

(b)J. Gernstein and W. P. Jenks, J. Am. Chem. Soc., 86, 4655 (1964),

(c)G. M. Steinberg and R. Swidler, J. Org. Chem., 30, 2362 (1965).

158.(a) B. Monzyk and A. L. Crumbliss, J. Org. Chem., 45, 4670 (1980),

(b)C. P. Brink and A. L. Crumbliss, J. Org. Chem., 47, 1171 (1982),

(c)C. P. Brink, L. L. Fish and A. L. Crumbliss, J. Org. Chem., 50, 2277 (1985).

159.F. G. Bordwell, H. E. Fried, D. L. Hughes, T. -Y. Lynch, A. V. Satish and Y. E. Whang, J. Org. Chem., 55, 3330 (1990).

160.M. Decouzon, O. Exner, J. -F. Gal and P. C. Maria, J. Org. Chem., 55, 3980 (1990).

161.(a) S. G. Lias, J. F. Libman and R. D. Levin, Chem Phys. Ref. Data, 13, 695 (1984),

(b) J. Catalan, J. L. G. De Paz, M. Yanez, R. M. Claramunt, C. Lopez, J. Elguero, F. Anvia,

J. H. Quian, M. Taagepera and R. W. Taft, J. Am. Chem. Soc., 112, 1303 (1990).

162.M. Meyer, J. Mol. Struct., 304, 45 (1994).

163.R. Krishnan, J. S. Binkley, R. Seeger and J. A. Pople, J. Chem. Phys., 72, 650 (1980).

164.B. Noszal and D. L. Rabenstein, J. Phys. Chem., 95, 4761 (1991).

165.(a) J. Catalan, M. Menendez and J. Elguero, Bull. Soc. Chim. Fr., I, 30 (1985),

(b) J. Catalan, J. L. M. Abboud and J. Elguero, Adv. Heterocycl. Chem., 41, 187 (1987).

166.J. Catalan, M. Sanchez-Cabezudo, J. L. G. De Paz and J. Elguero, Theochem J. Mol. Struct., 166, 415 (1988).

167.(a) C. H. DePuy, S. R. Kass and G. P. Bean, J. Org. Chem., 53, 4427 (1988),

(b) J. Catalan, J. L. G. De Paz, J. Elguero, A. Martinez, R. W. Taft and F. Anvia, Theochem J. Mol. Struct., 205, 367 (1990).

168. A. E. Tipping, P. Jiminez, E. Ballesteros, J. -L. M. Abboud, M. Yanez, M. Essefar and

J. Elguero, J. Org. Chem., 59, 1039 (1994).

169.(a) M. Balon, C. Carmona, J. Hidalgo, M. A. Munoz and P. Guardado, Heterocycles, 32, 1123 (1991),

(b) M. A. Munoz, P. Guardado, J. Hidalgo, C. Carmona and M. Balon, Tetrahedron, 48, 5901 (1992).

170.T. Brinck, J. S. Murray, P. Politzer and R. E. Carter, J. Org. Chem., 56, 2934 (1991).

171.A. R. Katriztky, Handbook of Heterocyclic Chemistry, Pergamon Press, New York, 1985, p. 302.

172. E. S. Lewis, in Supplement F: The Chemistry of Amino, Nitroso and Nitro Compounds (Ed.

S. Patai), Wiley, Chichester, 1982, pp. 715 729.

173.A. Pross and S. S. Shaik, J. Am. Chem. Soc., 104, 1129 (1982).

174.H. Yamataka and S. Nagase, J. Org. Chem., 53, 3232 (1988).

175.E. Grunwald, J. Am. Chem. Soc., 107, 125 (1985).

176.W. J. Albery, C. F. Bernasconi and A. J. Kresge, J. Phys. Org. Chem., 1, 29 (1988).

177.W. P. Jenks, Chem. Rev., 85, 511 (1985).

178.C. F. Bernasconi, Advances in Physical Organic Chemistry, Vol. 27, Academic Press, New York, 1992, pp. 1 238.

179.L. G. Arnaut, J. Phys. Org. Chem., 4, 726 (1991).

180.A. J. C. Varandas and S. J. Formosinho, J. Chem. Soc., Chem. Commun., 163 (1986).

183.F. G. Bordwell, J. C. Branca, D. L. Hughes and W. N. Olmstead, J. Org. Chem., 45, 3305 (1980).

184.C. F. Bernasconi and R. D. Bunnell, J. Am. Chem. Soc., 110, 2900 (1988).

185.E. M. Arnett, L. E. Small, D. Oancea and D. Johnston, J. Am. Chem. Soc., 98, 7346 (1976).

186.M. L. McKee, Chem. Phys. Lett., 164, 520 (1989).

187.(a) M. Sana, G. Leroy, D. Peeters and G. Wilante, J. Mol. Struct. Theochem, 164, 249 (1988),

(b) G. Leroy, M. Sana, G. Wilante and D. Peeters, J. Mol. Struct. Theochem, 187, 251 (1989).

188.J. B. Pedley, R. D. Naylor and S. P. Kirby, Thermochemical Data of Organic Compounds, 2nd ed., Chapman, New York, 1986.

189.E. Buncel and T. Durst, Comprehensive Carbanion Chemistry. Part A, Structure and Reactivity, Elsevier, Amsterdam, 1980, p.29.

190.K. E. Edgecombe and R. J. Boyd, Can. J. Chem., 62, 2887 (1984).

191.K. E. Edgecombe and R. J. Boyd, Can. J. Chem., 61, 45 (1983).

192.W. -K. Li, Croat. Chem. Acta, 63, 127 (1990).

193.J. E. Bartmess, J. A. Scott and R. T. Mclver, Jr., J. Am. Chem. Soc., 101, 6046 (1979).

194.J. Cioslowski, T. M. Stacey and E. D. Fleischmann, J. Am. Chem. Soc., 113, 4751 (1991).

195.J. Cioslowski, J. Phys. Rev. Lett., 62, 1469 (1969).

196.P. H. Boyle, M. A. Convery, A. P. Davis, G. D. Hosken and B. A. Murray, J. Chem. Soc., Chem. Commun., 3, 239 (1992).

197.G. Klebe, K. H. Bohn,¨ M. Marsch and G. Boche, Angew. Chem., Int. Ed. Engl., 26, 78 (1987).

198.F. G. Bordwell, J. C. Branca, D. L. Hughes and W. N. Olmstead, J. Org. Chem., 45, 3305 (1980).

199.V. G. Avakyan and O. V. Fateyev, Theochem J. Mol. Struct., 262, 39 (1992).

200.D. Barton and W. D. Ollis, in Comprehensive Organic Chemistry (Ed. I. O. Sutherland, ed.), Vol. 2, Pergamon Press, Oxford, 1979, pp. 335 336.

201.A. A. Kheir and J. F. Haw, J. Am. Chem. Soc., 116, 817 (1994).

202.E. Buncel and T. Durst, Comprehensive Carbanion Chemistry. Part A, Structure and Reactivity, Elsevier, Amsterdam, 1980, p. 323.

203.J. Lelievre, P. G. Farrell and F. Terrier, J. Chem. Soc., Perkin Trans. 2, 333 (1986).

204.C. F. Bernasconi, J. Org. Chem., 36, 1671 (1971).

205.F. G. Bordwel, D. Algrim and N. R. Vernier, J. Org. Chem., 42, 1817 (1977).

206.R. Schaal, J. Chim. Phys., 52, 796 (1955).

207.Terrier, J. Lelievre A. P. Chatrousse and P. G. Farrell, J. Chem. Soc., Perkin Trans. 2, 1479 (1985).

208.F. Terrier, H. -Q. Xie and P. G. Farrell, J. Org. Chem., 55, 2610 (1990).

209.P. G. Farrel, P. Fogel, A. P. Chatrousse, J. Lelievre and F. Terrier, J. Chem. Soc., Perkin Trans. 2, 51 (1985).

210.A. P. Chatrousse, F. Terrier, F. M. Fouad and P. G. Farrell, J. Chem. Soc., Perkin Trans. 2, 1243 (1979).

211.C. F. Bernasconi, D. A. V. Kliner, A. S. Mullin and J. X. Ni, J. Org. Chem., 53, 3342 (1988).

212.Terrier, H. Q. Xie, J. Lelievre, T. Boubaker and P. G. Farrel, J. Chem. Soc., Perkin Trans. 2, 1899 (1990).

213.D. N. Brooke and M. R. Crampton, J. Chem. Res., 10, 340 (1980).