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Azo coupling reactions structures and mechanisms

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Preparative Organic Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 112))

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5 References

  1. Zollinger, H.: Azo and Diazo Chemistry, New York-London, Interscience 1961

    Google Scholar 

  2. Kirmse, W.: Angew. Chem. 88, 273 (1976)

    Google Scholar 

  3. Kirmse, W., Baron, W. J., Seipp, U.: ibid. 85, 994 (1973)

    Google Scholar 

  4. Kirmse, W., Seipp, U.: Chem. Ber. 107, 745 (1974)

    Google Scholar 

  5. Kirmse, W., Schnurr, O., Jendralla, H.: ibid. 112, 2120 (1979)

    Google Scholar 

  6. Curtin, D. Y., Klanderman, B. H., Tavares, D. F.: J. Org. Chem. 27, 2709 (1962)

    Google Scholar 

  7. Lunt, R. S. III.: Dissert. Abstr. 29, 3108-B (1968–9)

    Google Scholar 

  8. Scherer, K. V.: private communication

    Google Scholar 

  9. Scherer, K. V., Lunt, R. S. III.: J. Am. Chem. Soc. 88, 2860 (1966)

    Google Scholar 

  10. Zwanenburg, B., Klunder, A. J. H.: Tetrahedron Lett. 1971, 1717

    Google Scholar 

  11. Kirmse, W., Schnurr, O.: J. Am. Chem. Soc. 99, 3539 (1977)

    Google Scholar 

  12. Reimlinger, H.: Angew. Chem. 75, 788 (1963)

    Google Scholar 

  13. Bott, K.: ibid. 76, 992 (1964)

    Google Scholar 

  14. Bott, K.: Chem. Ber. 108, 402 (1975)

    Google Scholar 

  15. Saalfrank, R. W., Ackermann, E.: Liebigs Ann. Chem. 1981, 7

    Google Scholar 

  16. Saalfrank, R. W., Ackermann, E.: Chem. Ber. 114, 3456 (1981)

    Google Scholar 

  17. Szele, I., Tencer, M., Zollinger, H.: Helv. Chim. Acta 66, in print (1983)

    Google Scholar 

  18. Collman, J. P., Yamada, M.: J. Org. Chem. 28, 3017 (1963)

    Google Scholar 

  19. Helwig, R.: Ph. D. Thesis, University of Tübingen

    Google Scholar 

  20. Huisgen, H.: Angew. Chem. 67, 439 (1955)

    Google Scholar 

  21. Staudinger, H., Meyer, J.: Helv. Chim. Acta 2, 619 (1919)

    Google Scholar 

  22. Wittig, G., Haag, W.: Chem. Ber. 88, 1654 (1955)

    Google Scholar 

  23. Coleman, G. H., Gilman, H., Adams, C. E., Pratt, P. E.: J. Org. Chem. 3, 99 (1938)

    Google Scholar 

  24. Regitz, M., Heck, G.: Chem. Ber. 97, 1482 (1964)

    Google Scholar 

  25. Kaiser, E. M., Warner, C. D.: J. Organomet. Chem. 31, C17 (1971)

    Google Scholar 

  26. Wenkert, E., McPherson, C. A.: J. Am. Chem. Soc. 94, 8084 (1972)

    Google Scholar 

  27. Müller, E., Huber-Emden, H.: Liebigs Ann. Chem. 660, 54 (1962)

    Google Scholar 

  28. Severin, T.: Angew. Chem. 70, 745 (1958)

    Google Scholar 

  29. Eisert, B., Greiber, B., Caspari, I.: Liebigs Ann. Chem. 659, 72 (1962)

    Google Scholar 

  30. Eisert, B., Regitz, M., Heck, G., Schall, H. in: Methoden der organischen Chemie (Houben-Weyl), 4th ed., Vol. X/4, p. 873, Stuttgart, Georg Thieme Verlag 1968

    Google Scholar 

  31. Ciganek, E.: J. Org. Chem. 30, 4198 (1965)

    Google Scholar 

  32. Schönberg, A., Junghans, K.: Chem. Ber. 98, 820 (1965)

    Google Scholar 

  33. Nesnow, S., Shapiro, R.: J. Org. Chem. 34, 2011 (1969)

    Google Scholar 

  34. Hartke, K., Uhde, W.: Tetrahedron Lett. 1969, 1697

    Google Scholar 

  35. Schmiechen, R.: ibid. 1969, 4995

    Google Scholar 

  36. Pyrek, J. S., Achmatowicz, Jr., O.: ibid. 1970, 2651

    Google Scholar 

  37. Huisgen, R., Reissig, H.-U., Voss, S.: ibid. 1979, 2987

    Google Scholar 

  38. Huisgen, R.: Angew. Chem. 75, 742 (1963)

    Google Scholar 

  39. Huisgen, R.: J. Org. Chem. 33, 2291 (1968)

    Google Scholar 

  40. Schöllkopf, U., Wiskott, E., Riedel, K.: Liebigs Ann. Chem. 1975, 387

    Google Scholar 

  41. IUPAC Nomenclature of Organic Chemistry (eds.) Rigaudy, J., Klesney, S. P., Oxford, Pergamon Press 1979

    Google Scholar 

  42. Kazitsyna, L. A., Klyueva, M. D.: Dokl. Akad. Nauk SSSR 204, 99 (1972)

    Google Scholar 

  43. Ershov, V. V., Nikiforov, G. A., de Jonge, C. R. H. I.: Quinonediazides, Studies in Organic Chemistry 7, Amsterdam-Oxford-New York, Elsevier 1981

    Google Scholar 

  44. Allan, Z., Podstata, J.: Tetrahedron Lett. 1967, 1911

    Google Scholar 

  45. Allan, Z., Podstata, J.: Collect. Czech. Chem. Commun. 34, 125 (1969)

    Google Scholar 

  46. Kazitsyna, L. A., Klyueva, M. D., Romanova, K. V.: Dokl. Akad. Nauk SSSR 183, 105 (1968)

    Google Scholar 

  47. Nikiforov, G. A., Plekhanova, L. G., Efremenko, A. A., Pobedimski, D. G., Ershov, V. V.: Izv. Akad. Nauk SSSR, Ser. Khim. 1971, 146

    Google Scholar 

  48. Huisgen, R., Fleischmann, R.: Liebigs Ann. Chem. 623, 47 (1959)

    Google Scholar 

  49. Schulz, R., Schweig, A.: Angew. Chem. 91, 737 (1979)

    Google Scholar 

  50. Reference 1, p. 41, 153

    Google Scholar 

  51. Ried, W., Dietrich, R.: Liebigs Ann. Chem. 666, 113 (1963)

    Google Scholar 

  52. Ried, W., Wagner, K.: ibid. 681, 45 (1965)

    Google Scholar 

  53. Ried, W., Kraemer, R.: ibid. 681, 52 (1965)

    Google Scholar 

  54. Ried, W., Junker, P.: ibid. 709, 85 (1967)

    Google Scholar 

  55. Reference 1, p. 215

    Google Scholar 

  56. Weaver, M. A., Shuttleworth, L.: Dyes and Pigments 3, 81 (1982)

    Google Scholar 

  57. Butler, R. N.: Chem. Rev. 75, 241 (1975)

    Google Scholar 

  58. Štěrba, V.: Diazonium-Diazo Equilibrium, in: The Chemistry of Diazonium and Diazo Groups (ed. Patai, S.), p. 84, Chichester, John Wiley & Sons 1978

    Google Scholar 

  59. Sawaguchi, H., Hashida, Y., Matsui, K.: Kogyo Kagaku Zasshi 74, 1859 (1971)

    Google Scholar 

  60. Butler, R. N., Scott, F. L.: J. Org. Chem. 32, 1224 (1967)

    Google Scholar 

  61. Hattori, K., Lieber, E., Horowitz, J. P.: J. Am. Chem. Soc. 78, 411 (1956)

    Google Scholar 

  62. Horowitz, J. P., Grakauskas, V. A.: J. Am. Chem. Soc. 79, 1249 (1957)

    Google Scholar 

  63. Gehlen, H., Dost, J.: Liebigs Ann. Chem. 655, 144 (1963)

    Google Scholar 

  64. Tedder, J. M.: Adv. Heterocycl. Chem. 8, 1 (1967)

    Google Scholar 

  65. Reimlinger, H., van Overstraeten, A.: Chem. Ber. 99, 3350 (1966)

    Google Scholar 

  66. Reimlinger, H., Merenyi, R.: ibid. 103, 3284 (1970)

    Google Scholar 

  67. Reimlinger, H., King, G. S. D., Peiren, M. A.: ibid. 103, 2821 (1970)

    Google Scholar 

  68. Simonov, A. M., Andreichikov, Yu. P.: Zh. Org. Khim. 5, 779 (1969)

    Google Scholar 

  69. Spiliadis, A., Bretcann, D., Eftimescu, C., Schip, R. T.: Romanian Pat. 50786 (1968); Chem. Abstr. 70, 4114h (1969)

    Google Scholar 

  70. Pan'kov, A. K., Pevsner, M. S., Bagal, L. I.: Khim. Geterotsikl. Soedin. 1972, 713

    Google Scholar 

  71. Wieland, H.: Liebigs Ann. Chem. 328, 197 (1903)

    Google Scholar 

  72. Goerdeler, J., Haubrich, H.: Chem. Ber. 93, 397 (1960)

    Google Scholar 

  73. Stevenson, H. B., Johnson, J. R.: J. Am. Chem. Soc. 59, 2525 (1937)

    Google Scholar 

  74. Putokhin, N. I., Yakovlev, V. I.: Sb. Nauchn. Tr. Kuibyshev: Ind. Inst. 1953, 175

    Google Scholar 

  75. Albert, A.: Heterocyclic Chemistry, pp. 80–85, London, Athlone Press, 1968

    Google Scholar 

  76. Kalatzis, E.: J. Chem. Soc. B, 1967, 273

    Google Scholar 

  77. Henricksen, L., Antrup, H.: Acta Chem. Scand. 26, 3342 (1972)

    Google Scholar 

  78. Kolodyazhnaya, S. N., Simonov, A. M., Zheltikova, N. N., Pozharskii, A. F.: Khim. Geterotsikl. Soedin. 1973, 714

    Google Scholar 

  79. Temple, C., Kussner, C. L., Motgomery, J. A.: J. Org. Chem. 32, 2241 (1967)

    Google Scholar 

  80. Tišler, M., Stanovnik, B.: Heterocycles 4, 1115 (1976)

    Google Scholar 

  81. Sheppard, W. A., Webster, O. W.: J. Am. Chem. Soc. 95, 2695 (1973)

    Google Scholar 

  82. Hünig, S., Boes, O.: Liebigs Ann. Chem. 579, 28 (1953)

    Google Scholar 

  83. Macháček, V., Panchartek, J., Štěrba, V., Večeřa, M.: Collect. Czech. Chem. Commun. 33, 3154 (1968)

    Google Scholar 

  84. Macháček, V., Panchartek, J., Štěrba, V., Večeřa, M.: ibid. 35, 844 (1970)

    Google Scholar 

  85. Macháček, V., Macháčková, O., Štěrba, V.: ibid. 35, 2954 (1970)

    Google Scholar 

  86. Macháček, V., Panchartek, J., Štěrba, V.: ibid. 35, 3410 (1970)

    Google Scholar 

  87. Macháček, V., Macháčková, O., Štěrba, V.: ibid. 36, 3187 (1971)

    Google Scholar 

  88. Reference 1, pp. 199–210

    Google Scholar 

  89. Wulfman, D. S.: Synthetic Applications of Diazonium Ions, in: The Chemistry of Diazonium and Diazo Groups (ed. Patai, S.), pp. 268–274, Chichester, John Wiley & Sons 1978

    Google Scholar 

  90. Hegarty, A. F.: Kinetics and Mechanisms of Reactions Involving Diazonium and Diazo Groups, in: The Chemistry of Diazonium and Diazo Groups (ed. Patai, S.), pp. 543–545, Chichester, John Wiley & Sons 1978

    Google Scholar 

  91. Enders, E., Pütter, R.: Methoden zur Herstellung und Umwandlung von Formazanen, in: Methoden der Organischen Chemie (Houben-Weyl), Vol. X/3, pp. 467, 627, Stuttgart, Georg Thieme Verlag 1965

    Google Scholar 

  92. Yao, H. C., Resnick, P.: J. Am. Chem. Soc. 84, 3514 (1962)

    Google Scholar 

  93. Curtin, D. Y., Poutsma, M. L.: ibid. 84, 4887 (1962)

    Google Scholar 

  94. Wahl, H., Lebris, M. T.: Bull. Soc. Chim. Fr. 1952, 436

    Google Scholar 

  95. Wahl, H., Lebris, M. T.: ibid. 1954, 1281

    Google Scholar 

  96. Lebris, M. T., Wahl, H.: ibid. 1954, 248

    Google Scholar 

  97. Behr, L. C.: Indazoles and Condensed Types, in: The Chemistry of Heterocyclic Compounds 22 (ed. Wiley, R. H.), p. 295, New York-London-Sydney, Interscience 1967

    Google Scholar 

  98. Huisgen, R., Nakaten, H.: Liebigs Ann. Chem. 586, 84 (1954)

    Google Scholar 

  99. Tröndlin, F., Werner, R., Rüchardt, C.: Chem. Ber. 111, 367 (1978)

    Google Scholar 

  100. Reference 89, p. 273

    Google Scholar 

  101. Curtin, D. Y., Tveten, J. L.: J. Org. Chem. 26, 1764 (1961)

    Google Scholar 

  102. Ainley, A. D., Robinson, R.: J. Chem. Soc. 1937, 369

    Google Scholar 

  103. Dyatkin, B. L., Zhuravkova, L. G., Martynov, B. I., Sterlin, S. R., Knunyants, I. L.: J. Chem. Soc., Chem. Commun. 1972, 618

    Google Scholar 

  104. Schwander, H. R.: Dyes and Pigments 3, 133 (1982)

    Google Scholar 

  105. Hung, M.-H., Stock, L. M.: J. Org. Chem. 47, 448 (1982)

    Google Scholar 

  106. Chin, A., Hung, M.-H., Stock, L. M.: ibid. 46, 2203 (1981)

    Google Scholar 

  107. Park, K. K., Archer, M. C., Wishnok, J. S.: Chem. Biol. Interact. 29, 139

    Google Scholar 

  108. Hocking, J. D., Harris, J. I.: FEBS Lett. 34, 280 (1973)

    Google Scholar 

  109. Butler, A. R., Pogorzelec, P., Shepherd, P. T.: J. Chem. Soc., Perkin II, 1977, 1452

    Google Scholar 

  110. Butler, A. R., Shepherd, P. T.: J. Chem. Research 1978, (S) 339 and (M) 4471

    Google Scholar 

  111. Butler, A. R., Shepherd, P. T.: J. Chem. Soc., Perkin II 1980, 113

    Google Scholar 

  112. Schofield, K.: Heteroaromatic Nitrogen Compounds, p. 76, London, Butterworths 1967

    Google Scholar 

  113. Gossauer, A.: Die Chemie der Pyrrole, p. 105, Berlin, Springer 1974

    Google Scholar 

  114. Gore, S. T., Mackie, R. K., Tedder, J. M.: J. Chem. Soc., Perkin I 1976, 1639

    Google Scholar 

  115. Challis, B. C., Rzepa, H. S.: J. Chem. Soc., Perkin II 1975, 1209

    Google Scholar 

  116. Genkina, M. K., Eraksina, V. N., Shagalov, L. B., Suvorov, N. N.: Zh. Org. Khim. 15, 2530 (1979)

    Google Scholar 

  117. Genkina, N. K., Mirzametova, R. M., Buyanov, V. N., Suvorov, N. N.: ibid. 17, 667 (1981)

    Google Scholar 

  118. Sarma, P. K., Barooah, S. K.: Indian J. Chem. 15B, 382 (1977)

    Google Scholar 

  119. Spande, T. F., Glenner, G. G.: J. Am. Chem. Soc. 95, 3400 (1973)

    Google Scholar 

  120. Wittwer, Ch., Zollinger, H.: Helv. Chim. Acta 37, 1954 (1954)

    Google Scholar 

  121. Kropáčova, H., Panchartek, J., Štěrba, V., Valter, K.: Collect. Czech. Chem. Commun. 35, 3287 (1970)

    Google Scholar 

  122. Fischer, P. B., Zollinger, H.: Helv. Chim. Acta 55, 2139 (1972)

    Google Scholar 

  123. Fischer, P. B., Zollinger, H.: ibid. 55, 2146 (1972)

    Google Scholar 

  124. Reference 1, p. 178

    Google Scholar 

  125. Jaecklin, A. P., Skrabal, P., Zollinger, H.: ibid. 54, 2870 (1971)

    Google Scholar 

  126. Bradley, W., Thompson, J. D.: Nature 178, 1069 (1956)

    Google Scholar 

  127. Messmer, A., Szimán, O.: Angew. Chem. 79, 237 (1967)

    Google Scholar 

  128. Penton, J. R., Zollinger, H.: Helv. Chim. Acta 54, 573 (1971)

    Google Scholar 

  129. Gutman, V.: Chimia 31, 1 (1977)

    Google Scholar 

  130. Bagal, I. L., Skvortsov, S. A., El'tsov, A. V.: Zh. Org. Khim. 14, 361 (1978)

    Google Scholar 

  131. Hashida, Y., Ishida, H., Sekiguchi, S., Matsui, K.: Bull. Chem. Soc. Jpn. 47, 1224 (1974)

    Google Scholar 

  132. Hashida, Y., Tanabe, F., Sekiguchi, S., Matsui, K.: Nippon Kagaku Kaishi 1975, 1761

    Google Scholar 

  133. Hashida, Y., Fujinuma, K., Aikawa, K.: ibid. 1975, 1369

    Google Scholar 

  134. Hashida, Y., Tanabe, F., Matsui, K.: ibid. 1980, 865

    Google Scholar 

  135. Juri, P. N., Bartsch, R. A.: J. Org. Chem. 44, 143 (1979)

    Google Scholar 

  136. Szimán, O., Messmer, A.: Tetrahedron Lett. 1968, 1625

    Google Scholar 

  137. Poindexter, M., McKay, B.: J. Org. Chem. 37, 1674 (1972)

    Google Scholar 

  138. Rufer, D. A.: Ph. D. Thesis, ETH Zurich 1981

    Google Scholar 

  139. Hashida, Y., Matsumura, K., Ohmori, Y., Matsui, K.: Nippon Kagaku Kaishi 1979, 1745

    Google Scholar 

  140. Moss, R. A., Rav-Acha, C.: J. Am. Chem. Soc. 102, 5045 (1980)

    Google Scholar 

  141. Zollinger, H.: Helv. Chim. Acta 36, 1723 (1953)

    Google Scholar 

  142. Gokel, G. W., Cram, D. J.: J. Chem. Soc., Chem. Commun. 1973, 481

    Google Scholar 

  143. Kyba, E. P., Helgeson, R. C., Madan, K., Gokel, G. W., Tarnowski, T. L., Moore, S. S., Cram, D. J.: J. Am. Chem. Soc. 99, 2564 (1977)

    Google Scholar 

  144. Korzeniowski, S. H., Gokel, G. W.: Tetrahedron Lett. 1977, 1637

    Google Scholar 

  145. Ahern, M. F., Gokel, G. W.: J. Chem. Soc., Chem. Commun. 1979, 1019

    Google Scholar 

  146. Szele, I., Zollinger, H.: Helv. Chim. Acta 61, 1721 (1978)

    Google Scholar 

  147. Ellwood, M., Griffiths, J.: J. Chem. Soc., Chem. Commun. 1980, 181

    Google Scholar 

  148. Ellwood, M., Gregory, P., Griffiths, J.: Eur. Pat. Appl. 28, 464 (Oct. 8, 1980); Chem. Abstr. 95 P 134370r (1981)

    Google Scholar 

  149. Kobayashi, H., Sonoda, T., Iwamoto, H.: Chem. Lett. 1981, 579

    Google Scholar 

  150. Conant, J. B., Peterson, W. D.: J. Am. Chem. Soc. 52, 1220 (1930)

    Google Scholar 

  151. Wistar, R., Bartlett, P. D.: ibid. 63, 413 (1941)

    Google Scholar 

  152. Pütter, R.: Angew. Chem. 63, 188 (1951)

    Google Scholar 

  153. Zollinger, H., Wittwer, C.: Helv. Chim. Acta 35, (1952)

    Google Scholar 

  154. Zollinger, H.: ibid. 39, 1600 (1956)

    Google Scholar 

  155. Allan, Z. J.: Collect. Czech. Chem. Commun. 16, 620 (1951)

    Google Scholar 

  156. Zollinger, H.: Helv. Chim. Acta 36, 1070 (1953)

    Google Scholar 

  157. Kaválek, J., Panchartek, J., Štěrba, V., Valter, K.: Collect. Czech. Chem. Commun. 35, 3470 (1970)

    Google Scholar 

  158. Štěrba, V., Valter, K.: ibid. 37, 270 (1972)

    Google Scholar 

  159. Macháčková, O., Štěrba, V., Valter, K.: ibid. 37, 1851 (1972)

    Google Scholar 

  160. Cox, A., Goodman, P. D., Kemp, T. J., de Moira, P., Pinot, P.: Int. J. Chem. Kinet. 13, 97 (1981)

    Google Scholar 

  161. Dobáš, I., Štěrba, V., Večeřa, M.: Collect. Czech. Chem. Commun. 34, 3905 (1969)

    Google Scholar 

  162. Mitsumura, K., Hashida, Y., Sekiguchi, S., Matsui, K.: Bull. Chem. Soc. Jpn. 46, 1770 (1973)

    Google Scholar 

  163. Hashida, Y., Mitsumura, K., Sekiguchi, S., Matsui, K.: ibid. 46, 3263 (1973)

    Google Scholar 

  164. Reference 1, p. 213

    Google Scholar 

  165. Hashida, Y., Kobayashi, M., Matsui, K.: Bull. Chem. Soc. Jpn. 44, 2506 (1971)

    Google Scholar 

  166. Schwarzenbach, G., Felder, E.: Helv. Chim. Acta 27, 1701 (1944)

    Google Scholar 

  167. Hashida, Y., Shimoda, I., Sekiguchi, S., Matsui, K.: Kogyo Kagaku Zasshi 74, 73 (1971)

    Google Scholar 

  168. Dobáš, I., Štěrba, V., Večeřa, M.: Collect. Czech. Chem. Commun. 34, 3895 (1969)

    Google Scholar 

  169. Macháček, V., Panchartek, J., Stěrba, V., Tunka, J.: ibid. 33, 3579 (1968)

    Google Scholar 

  170. Noelting, E., Grandmougin, E.: Bull. Soc. Chim. Fr. 1891, 873

    Google Scholar 

  171. Noelting, E., Grandmougin, E.: Ber. Dtsch. Chem. Ges. 24, 1601 (1891)

    Google Scholar 

  172. Hanna, S. B., Hunziker, E., Saito, T., Zollinger, H.: Helv. Chim. Acta 52, 1537 (1969)

    Google Scholar 

  173. Hunziker, E., Penton, J. R., Zollinger, H.: ibid. 54, 2043 (1971)

    Google Scholar 

  174. Zollinger, H.: Chimia 27, 186 (1973)

    Google Scholar 

  175. Ott, R. J., Rys, P.: Helv. Chim. Acta 58, 2074 (1975)

    Google Scholar 

  176. Nabholz, F., Ott, R. J., Rys, P.: ibid. 60, 2926 (1977)

    Google Scholar 

  177. Nabholz, F., Rys, P.: ibid. 60, 2937 (1977)

    Google Scholar 

  178. Bourne, J. R., Crivelli, E., Rys, P.: ibid. 60, 2944 (1977)

    Google Scholar 

  179. Belevi, H., Bourne, J. R., Rys, P.: ibid. 64, 1599 (1981)

    Google Scholar 

  180. Belevi, H., Bourne, J. R., Rys, P.: ibid. 64, 1618 (1981)

    Google Scholar 

  181. Belevi, H., Bourne, J. R., Rys, P.: ibid. 64, 1630 (1981)

    Google Scholar 

  182. Besse, J., Schwarz, W., Zollinger, H.: ibid. 64, 502 (1981)

    Google Scholar 

  183. Schwarz, W., Zollinger, H.: ibid. 64, 513 (1981)

    Google Scholar 

  184. Besse, J., Zollinger, H.: ibid. 64, 529 (1981)

    Google Scholar 

  185. Kaválek, J., Panchartek, J., Štěrba, V.: Collect. Czech. Chem. Commun. 35, 3470 (1970)

    Google Scholar 

  186. Zollinger, H.: Helv. Chim. Acta 38, 1597 (1955)

    Google Scholar 

  187. Zollinger, H.: ibid. 38, 1617 (1955)

    Google Scholar 

  188. Zollinger, H.: ibid. 38, 1623 (1955)

    Google Scholar 

  189. Melander, L.: Arkiv Kemi 2, 213 (1950)

    Google Scholar 

  190. Berglund-Larsson, U., Melander, L.: ibid. 6, 219 (1953)

    Google Scholar 

  191. Hammond, G. S.: J. Am. Chem. Soc. 77, 2444 (1955)

    Google Scholar 

  192. Snyckers, F., Zollinger, H.: Helv. Chim. Acta 53, 1294 (1970)

    Google Scholar 

  193. Binks, J. H., Ridd, J. H.: J. Chem. Soc. 1957, 2398

    Google Scholar 

  194. Rys, P., Skrabal, P., Zollinger, H.: Angew. Chem. 84, 921 (1972), Angew. Chem. Intern. Ed. 11, 874 (1972)

    Google Scholar 

  195. Geidysh, L. S., Nikiforov, G. A., Ershov, V. V.: Izv. Akad. Nauk SSSR, Ser. Khim. 1969, 2716

    Google Scholar 

  196. Zollinger, H.: Acc. Chem. Res. 6, 335 (1973)

    Google Scholar 

  197. Jermini, C., Koller, S., Zollinger, H.: Helv. Chim. Acta 53, 72 (1970)

    Google Scholar 

  198. Duthaler, R. O., Förster, H. G., Roberts, J. D.: J. Am. Chem. Soc. 100, 4974 (1978)

    Google Scholar 

  199. Hanna, S. B., Jermini, C., Zollinger, H.: Tetrahedron Lett. 1969, 4415

    Google Scholar 

  200. Hanna, S. B., Jermini, C., Loewenschuss, H., Zollinger, H.: J. Am. Chem. Soc. 96, 7222 (1974)

    Google Scholar 

  201. Schowen, R. L.: Progr. Phys. Org. Chem. 9, 275 (1972)

    Google Scholar 

  202. Stamm, O. A., Zollinger, H.: Helv. Chim. Acta 40, 1955 (1957)

    Google Scholar 

  203. Eigen, M.: Discuss. Faraday Soc. 39, 7 (1965)

    Google Scholar 

  204. Bell, R. P., Evans, P. G.: Proc. Roy. Soc. A 291, 297 (1966)

    Google Scholar 

  205. Bell, R. P.: Adv. Phys. Org. Chem. 4, 1 (1966)

    Google Scholar 

  206. Bell, R. P.: The Proton in Chemistry, pp. 122, 129, 186. London, Chapman and Hall 1973

    Google Scholar 

  207. Grunwald, E., Eustace, D.: Chapt. 4, in: Proton Transfer Reactions (ed. Caldin, E. F., Gold, V.), London, Chapman and Hall 1975

    Google Scholar 

  208. Williams, I. H., Spangler, D., Femec, D. A., Maggiora, G. M., Schowen, R. L.: J. Am. Chem. Soc. 102, 6619 (1980)

    Google Scholar 

  209. Williams, I. H., Spangler, D., Femec, D. A., Maggiora, G. M., Schowen, R. L.: ibid. 105, 31 (1983)

    Google Scholar 

  210. Demian, B.: Bull. Soc. Chim. Fr. 1973, 769

    Google Scholar 

  211. Demian, B.: Tetrahedron Lett. 1972, 3043

    Google Scholar 

  212. Hashida, Y., Katoka, S., Matsui, K.: Nippon Kagaku Kaishi 1975, 1213

    Google Scholar 

  213. Jencks, W. P.: Chem. Soc. Reviews 10, 345 (1981) and previous papers quoted there

    Google Scholar 

  214. Kishimoto, S., Kitahara, S., Manabe, O., Hiyama, H.: Nippon Kagaku Kaishi 1973, 1975

    Google Scholar 

  215. Kishimoto, S., Kitahara, S., Manabe, O., Hiyama, H.: ibid. 1974, 1962

    Google Scholar 

  216. Kishimoto, S., Kitahara, S., Manabe, O., Hiyama, H.: ibid. 1981, 428

    Google Scholar 

  217. Snyckers, F., Zollinger, H.: Tetrahedron Lett. 1970, 2759

    Google Scholar 

  218. Gloor, B., Zollinger, H.: Helv. Chim. Acta 54, 553 (1971)

    Google Scholar 

  219. Gloor, B., Zollinger, H.: ibid. 54, 563 (1971)

    Google Scholar 

  220. Brunning, W., Holtzer, A.: J. Am. Chem. Soc. 82, 4865 (1961)

    Google Scholar 

  221. Schick, M. J.: Phys. Chem. 68, 3585 (1964)

    Google Scholar 

  222. Hashida, Y., Nakajima, K., Sekiguchi, S., Matsui, K.: Kogyo Kagaku Zasshi 72, 1132 (1969)

    Google Scholar 

  223. Chmàtal, V., Allan, Z. J.: Collect. Czech. Chem. Commun. 30, 1205 (1965); see also references to patent literature in Gloor et al. 217)

    Google Scholar 

  224. Clemson, A., Symons, C., Rezakhani, S., Whiting, M. C.: J. Chem. Res. (S) 1980, 162

    Google Scholar 

  225. Koller, S., Zollinger, H.: Helv. Chim. Acta 53, 78 (1970)

    Google Scholar 

  226. Christen, M., Koch, W., Simon, W., Zollinger, H.: ibid. 45, 2077 (1962)

    Google Scholar 

  227. Bagal, I. L., Sire, L. E., El'tsov, A. V.: Zh. Org. Khim. 11, 1263 (1975)

    Google Scholar 

  228. Bubnov, N. N., Bilevitch, K. A., Poljakova, L. A., Okhlobystin, O. Yu.: J. Chem. Soc., Chem. Commun. 1972, 1058

    Google Scholar 

  229. Citterio, A., Minisci, F., Albinati, A., Bruckner, S.: Tetrahedron Lett. 1980, 2909

    Google Scholar 

  230. Citterio, A., Minisci, F.: J. Org. Chem. 47, 1759 (1982)

    Google Scholar 

  231. Citterio, A., Minisci, F., Vismara, E.: ibid., in press

    Google Scholar 

  232. Colonna, M., Greci, L., Poloni, M.: J. Chem. Soc., Perkin II 1982, 455

    Google Scholar 

  233. Jackson, A. H., Shannon, P. V. R., Tinker, A. C.: J. Chem. Soc., Chem. Commun. 1976, 796

    Google Scholar 

  234. Bisson, J. M., Hanson, P., Slocum, D.: J. Chem. Soc., Perkin II 1978, 1331

    Google Scholar 

  235. Penton, J. R., Zollinger, H.: Helv. Chim. Acta 64, 1728 (1981)

    Google Scholar 

  236. Shuttleworth, L.: Eastman Kodak, U.S. Pat. 4247458 (1981)

    Google Scholar 

  237. Beránek, U., Večeřa, M.: Collect. Czech. Chem. Commun. 34, 2753 (1969)

    Google Scholar 

  238. Beránek, U., Večeřa, M.: ibid. 35, 3402 (1970)

    Google Scholar 

  239. Bagal, I. L., Skvortsov, S. A., El'tsof, A. V.: Zh. Org. Khim. 14, 2244 (1978)

    Google Scholar 

  240. Penton, J. R., Zollinger, H.: J. Chem. Soc., Chem. Commun. 1979, 819

    Google Scholar 

  241. Penton, J. R., Zollinger, H.: Helv. Chim. Acta 64, 1717 (1981)

    Google Scholar 

  242. Arnett, E. M., Chwala, B., Bell, L., Taagepera, M., Hehre, W. J., Taft, R. W.: J. Am. Chem. Soc. 99, 5279 (1977)

    Google Scholar 

  243. Juri, P. N., Bartsch, R. A.: J. Org. Chem. 45, 2028 (1980)

    Google Scholar 

  244. Ogata, Y., Nakagawa, Y., Inaishi, M.: Bull. Chem. Soc. Jpn. 54, 2953 (1981)

    Google Scholar 

  245. Shine, H. J.: Aromatic Rearrangements, Chapter 3, New York, Elsevier 1967

    Google Scholar 

  246. Shine, H. J.: M.T.P. Reviews, Series One 3, 89 (1973)

    Google Scholar 

  247. Goldschmidt, H., Johnson, S., Overwien, E.: Z. Phys. Chem. 110, 251 (1924)

    Google Scholar 

  248. Reference 1, p. 185

    Google Scholar 

  249. Yamabe, T.: Bull. Chem. Soc. Jpn. 42, 3565 (1969)

    Google Scholar 

  250. Vogel, A. I.: Practical Organic Chemistry, p. 626, London, Longmans 1956

    Google Scholar 

  251. American Cyanamid, U.S. Pat. 4018751 (1975)

    Google Scholar 

  252. Kelly, R. P., Penton, J. R., Zollinger, H.: Helv. Chim. Acta 65, 122 (1982)

    Google Scholar 

  253. Sakla, A. B., Masoud, N. K., Sawiris, Z., Ebaid, W. S.: ibid. 57, 481 (1974)

    Google Scholar 

  254. Ball, P., Nicholls, C. H.: Dyes and Pigments 3, 5 (1982)

    Google Scholar 

  255. Zollinger, H.: Chemie der Azofarbstoffe, p. 217, Basel, Birkhäuser-Verlag 1958

    Google Scholar 

  256. Rys, P., Zollinger, H.: Fundamentals of the Chemistry and Applications of Dyes, p. 49, Chichester—New York, John Wiley 1972

    Google Scholar 

  257. Ikeda, T., Manabe, O., Hiyama, H.: Kogyo Kagaku Zasshi 70, 319 (1967)

    Google Scholar 

  258. Ikeda, T., Manabe, O., Hiyama, H.: ibid. 70, 323 (1967)

    Google Scholar 

  259. Ikeda, T., Manabe, O., Hiyama, H.: ibid. 70, 327 (1967)

    Google Scholar 

  260. Panchartek, J., Štěrba, V.: Collect. Czech. Chem. Commun. 34, 2971 (1969)

    Google Scholar 

  261. Kaminski, R., Lauk, U., Skrabal, P., Zollinger, H.: Helv. Chim. Acta 66, in print (1983)

    Google Scholar 

  262. Schneider, L.: Helv. Chim. Acta 51, 67 (1968)

    Google Scholar 

  263. Zollinger, H.: ibid. 36, 1730 (1953)

    Google Scholar 

  264. Bekkum, H. V., Verkade, P. E., Wepster, B. M.: Recl. Trav. Chim. Pays-Bas 78, 815 (1959)

    Google Scholar 

  265. Panchartek, J. Štěrba, V., Vorliček, J., Večeřa, M.: Collect. Czech. Chem. Commun. 33, 894 (1968)

    Google Scholar 

  266. Beránek, V., Kořinková, H., Vetešnik, P., Večeřa, M.: ibid. 37, 282 (1971)

    Google Scholar 

  267. Bagal, I. L., Skvortsov, S. A., El'tsov, A. V.: Zh. Org. Khim. 14, 361 (1978)

    Google Scholar 

  268. Remeš, M., Diviš, J., Zvěrina, V., Matrka, M.: Collect. Czech. Chem. Commun. 38, 1049 (1973)

    Google Scholar 

  269. Skvortsov, S. A., Barnakov, Ch. N., Bagal, I. L.: Zh. Org. Khim. 17, 133 (1981)

    Google Scholar 

  270. Ritchie, C. D., Wright, D. J.: J. Am. Chem. Soc. 93, 6574 (1971)

    Google Scholar 

  271. Brown, H. C., Stock, L. M.: ibid. 84, 3298 (1962)

    Google Scholar 

  272. Hoefnagel, A. J., Wepster, B. M.: ibid. 95, 5357 (1973)

    Google Scholar 

  273. Dobáš, I., Štěrba, V., Večeřa, M.: Chem. Ind. London 1968, 1814

    Google Scholar 

  274. Dobáš, I., Štěrba, V., Večeřa, M.: Collect. Czech. Chem. Commun. 34, 3746 (1969)

    Google Scholar 

  275. Dobáš, I., Panchartek, J., Štěrba, V., Večeřa, M.: ibid. 35, 1288 (1970)

    Google Scholar 

  276. Štěrba, V., Valter, K.: ibid. 37, 1327 (1972)

    Google Scholar 

  277. Kulič, J., Titz, M., Večeřa, M.: ibid. 40, 405 (1975)

    Google Scholar 

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  1. Technisch-Chemisches Laboratorium, Eidgenössische Technische Hochschule (ETH), CH-8092, Zürich, Switzerland

    Ivanka Szele & Heinrich Zollinger

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Szele, I., Zollinger, H. (1983). Azo coupling reactions structures and mechanisms. In: Preparative Organic Chemistry. Topics in Current Chemistry, vol 112. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-12396-2_5

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