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Oxidation of organic compounds at the nickel hydroxide electrode

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Electrochemistry I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 142))

Abstract

The nickel hydroxide electrode has proved to be a versatile, inexpensive and facile applicable reagent, that allows an easy scale-up of the oxidation. It furthermore exhibits a remarkable selectivity to oxidize the sterically less shielded functional group. It is to be expected, that further applications of the electrode will be developed, which are partly guided by experiences with nickel peroxide oxidations. Furthermore additional chemoselectivities may be found by the use of other transition metal oxide electrodes, e.g. copper-, silver- and cobalt oxide electrodes.

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8 References

  1. Organic Electrochemistry, (Baizer, M. M., Lund, H., ed.), M. Dekker 1983

    Google Scholar 

  2. Torii, S.: Electroorganic Syntheses, Part I, Monographs in Mod. Chemistry 15, Verlag Chemie 1985

    Google Scholar 

  3. Schäfer, H. J.: Angew. Chem. 93, 978 (1981); Angew. Chem. Internat. Ed. Engl. 20, 911 (1981)

    Google Scholar 

  4. Beck, F.: Elektroorganische Chemie, Verlag Chemie, 1974, pp. 142

    Google Scholar 

  5. Lit. 2) pp. 152

    Google Scholar 

  6. Lit. 1a) Chapt. 9–11

    Google Scholar 

  7. Lit. 2) pp. 177

    Google Scholar 

  8. Casanova, J., Eberson, L.: The Chemistry of the Carbon-Halogen bond (ed. Patai, S.), Wiley 1973, pp. 979

    Google Scholar 

  9. Lit. 1a) Chapt. 7, 22

    Google Scholar 

  10. Utley, J. H. P.: Top. Curr. Chem. in preparation (1987)

    Google Scholar 

  11. Montenegro, M. I.: Electrochim. Acta 31, 607 (1986)

    Article  Google Scholar 

  12. Lit. 2) pp. 196

    Google Scholar 

  13. Lit. 1b) Chapt. 8

    Google Scholar 

  14. Lit. 1a) Chapt. 15–17

    Google Scholar 

  15. Lit. 1a) Chapt. 23, 24

    Google Scholar 

  16. Lit. 1b) Chapt. 4

    Google Scholar 

  17. Lit. 1b) Chapt. 7

    Google Scholar 

  18. George, M. V., Balachandran, K. S.: Chem. Rev. 75, 491 (1975)

    Article  Google Scholar 

  19. Stecher, K. H.: Houben-Weyl „Methoden der Organischen Chemie“, Vol. 4/1b, Thieme Verlag, Stuttgart 1975, pp. 843

    Google Scholar 

  20. Ross, E.: Kontakte (Merck) 1979, 19

    Google Scholar 

  21. Weinberg, N. L., Weinberg, H. R.: Chem. Rev. 68, 449 (1968)

    Article  Google Scholar 

  22. Weinberg, N. L. (ed.): Technique of Electroorganic Synthesis, Part I, J. Wiley 1974, p. 435

    Google Scholar 

  23. Seiler, P., Robertson, P. M.: Chimia 36, 305 (1982)

    Google Scholar 

  24. Fleischmann, M., Korinek, K., Pletcher, D.: J. Chem. Soc. Perkin Trans. II, 1396 (1972)

    Google Scholar 

  25. Vertes, G., Horanyi, G., Nagy, F.: Tetrahedron 28, 37 (1972)

    Article  Google Scholar 

  26. Vertes, G., Horanyi, G., Nagy, F.: Acta Chim. Acad. Sci. Hung. 67, 145 (1971); 68, 217 (1971)

    Google Scholar 

  27. Remorov, B. S., Avrutskaya, I. A., Fioshin, M. Y.: Electrokhimiya 17, 743 (1981); Chem. Abstr. 95, 32564q (1981); 17, 1547 (1981); Chem. Abstr. 95, 227804a (1981)

    Google Scholar 

  28. Remorov, B. S., Avrutskaya, I. A., Fioshin, M. Y.: Elektrokhimiya 16, 723 (1980); Chem. Abstr. 93, 56661 d (1980)

    Google Scholar 

  29. Kaulen, J., Schäfer, H. J.: Synthesis 1979, 513

    Google Scholar 

  30. Kaulen, J., Schäfer, H. J.: Tetrahedron 38, 3299 (1982)

    Article  Google Scholar 

  31. Fioshin, M. Y., Avrutskaya, I. A., Remorov, B. S., Remorova, N. A.: Elektrokhimiya 18, 678 (1982); Chem. Abstr. 97, 62940t (1982)

    Google Scholar 

  32. Fioshin, M. Y.: Russ. Pat., Chem. Abstr. 105, 31928 (1986)

    Google Scholar 

  33. Rudik, I. V., Avrutskaya, I. A., Fioshin, M. Y.: Elektrokhimiya 22, 1081 (1986); Chem. Abstr. 105, 180379y (1986)

    Google Scholar 

  34. Lit. 11), ref. 42–47

    Google Scholar 

  35. Mulina, T. E., Avrutskaya, I. A., Fioshin, M. Y.: Elektrokhimiya 10, 481 (1974); Chem. Abstr. 81, 32499h (1974)

    Google Scholar 

  36. Lidorenko, N. S., Fioshin, M. Y., Muchnik, G. F., Serebryanskii, V. T., Avrutskaya, I. A., Khrizolitova, M. A., Rodionova, N. A.: Elektrokhimya 16, 750 (1980); Chem. Abstr. 93, 56663 (1980)

    Google Scholar 

  37. Horanyi, G., Vertes, G., Nagy, F.: Acta Chim. (Budapest) 67, 357 (1971); Chem. Abstr. 74, 119374t (1971)

    Google Scholar 

  38. Vertes, G., Horanyi, G., Nagy, F.: Croat. Chem. Acta 44, 21 (1972); Chem. Abstr. 77, 28185 (1972)

    Google Scholar 

  39. Briggs, G. W. D., Jones, E., Wynne-Jones, W. F. K.: Trans. Faraday Soc. 51, 1433 (1955)

    Article  Google Scholar 

  40. Robertson, P. M., Berg, P., Reimann, H., Schleich, K., Seiler, P.: J. Electrochem. Soc. 130, 591 (1983)

    Google Scholar 

  41. Pechatnova, T. E., Mairov, A. P., Avrutskaya, I. A., Fioshin, M. Y., Kazarinov, V. E.: Elektrokhimiya 14, 1246 (1978); Chem. Abstr. 89, 186476a (1978)

    Google Scholar 

  42. Avrutskaya, I. A., Fioshin, M. Y., Mulinov, T. E., Arkhipova, T. A.: Elektrokhimiya 11, 1260 (1975); Chem. Abstr. 84, 23697f (1976)

    Google Scholar 

  43. Trivedi, D. C., Udupa, K. S., Udupa, H. V. K.: Proc. Indian Natl. Sci. Acad., Part A 48, 333 (1982); Chem. Abstr. 98, 169227p (1983); Manandhar, K., Pletcher, D.: J. Appl. Electrochem. 9, 707 (1979); Chem. Abstr. 92, 30959m (1980); McDougall, B., Graham, M. J.: J. Electrochem. Soc. 128, 2321 (1981); Burshtein, R. Kh., Kazarinov, V. E., Pshenichnikov, A. G., Barbasheva, I. E., Kuzmicheva, O. A.: Russ. Pat., Chem. Abstr. 103, 112236h (1985)

    Google Scholar 

  44. Krishtalik, L. I., Morozov, A. M., Mostkova, R. I., Vilinskaya, V. S., Klynkhina, N. M., Tedoradze, G. A.: Russ. Pat., Chem. Abstr. 101, 13751t (1984)

    Google Scholar 

  45. Ferrando, W. A.; J. Electrochem. Soc. 132, 2417 (1985)

    Google Scholar 

  46. Mrha, J., Klapste, B., Zabransky, Z., Micka, K., Wiczek, B., Vyskovsky, O.: Czech. Pat., Chem. Abstr. 103, 168731h (1985)

    Google Scholar 

  47. Mrha, J., Kreyci, I., Klapste, B., Braunstein, B., Kondelka, V., Malik, J.: Power Sources 7, 153 (1978); Chem. Abstr. 92, 25469 (1979)

    Google Scholar 

  48. Ezhov, B. B., Malandin, O. G., Rakhovskaya, S. M.: Elektrokhimiya 20, 140 (1984); Chem. Abstr. 100, 128672w (1984)

    Google Scholar 

  49. Folquar, M. E., Vilche, J. R., Arvia, A. J.: An. Asoc. Quim. Argent. 70, 873 (1982); Chem. Abstr. 98, 9447g (1983)

    Google Scholar 

  50. The “Swiss-roll” cell is commercially available from: Dr. Robertson, P. M., Haldenstr. 9, 8185 Winkel, Switzerland

    Google Scholar 

  51. Bomberger, D. C., Feldmann, D., Moose, L. F.: Chem.-Ing.-Tech. 38, 665 (1966); v. Sturm, F.: Elektrochemische Stromerzeugung, Verlag Chemie, Weinheim 1969, pp. 45

    Article  Google Scholar 

  52. Weiniger, J. L., Breiter, M. W.: J. Electrochem. Soc. 110, 484 (1963)

    Google Scholar 

  53. Briggs, G. W. D., Snoden, P. R.: Electrochim. Acta 27, 565 (1982)

    Article  Google Scholar 

  54. Schrebler-Guzman, R. S., Vilche, J. R., Arvia, A. J.: J. Electrochem. Soc. 125, 1578 (1978)

    Google Scholar 

  55. Visscher, W., Barendrecht, E.: J. Electroanal. Chem. 154, 69 (1983)

    Article  Google Scholar 

  56. Barnard, R., Randell, C. F.: J. Appl. Electrochem. 13, 97 (1983); Chem. Abstr. 98, 80455p (1983) and earlier lit. of these authors

    Article  Google Scholar 

  57. Bode, H., Dehmelt, K., Witte, J.: Z. Anorg. Allg. Chem. 366, 1 (1969)

    Article  Google Scholar 

  58. Beden, B., Floner, D., Leger, J. M., Lamy, C.: Surf. Sci. 162, 822 (1985); Chem. Abstr. 104, 12202w (1986)

    Article  Google Scholar 

  59. Briggs, G. W., Specialist Periodical Reports-Electrochemistry, Vol. 4. Chemical Society, London 1974, p. 33

    Google Scholar 

  60. Oliva, P., Leonardi, J., Faurent, F. J., Delmas, C., Braconnier, J. J., Figlarz, M., Fievet, F., De Guibert, A.: J. Power Sources 8, 229 (1982)

    Article  Google Scholar 

  61. Greaves, C., Malsbury, A. M., Thomas, M. A.: Solid State lonics 18 + + 19, 763 (1986)

    Google Scholar 

  62. Tanabe, H., Fukushima, S.: Electrochim. Acta 29, 1173 (1984)

    Article  Google Scholar 

  63. Greaves, C., Thomas, M. A., Turner, M.: J. Power Sources 12, 195 (1984); Chem. Abstr. 100, 217805j (1984)

    Article  Google Scholar 

  64. Carbonio, R. E., Macagno, V. A., Arvia, A. J.: J. Electroanal. Chem. 147, 139 (1983)

    Article  Google Scholar 

  65. Beden, B., Croissant, M. J., Lamy, C., Hahn, F.: Electrochim. Acta 31, 335 (1986)

    Article  Google Scholar 

  66. Melendres, C. A., Xu, S.: J. Electrochem. Soc. 131, 2239 (1984)

    Google Scholar 

  67. McEwen, R. S.: J. Phys. Chem. 75, 1782 (1972)

    Article  Google Scholar 

  68. Bode, H., Dehmelt, K., Witte, J.: Z. Anorg. Allg. Chem. 366, 1 (1969)

    Article  Google Scholar 

  69. Conway, B. E., Sattar, M. A.: J. Electroanal. Chem. 19, 351 (1968)

    Article  Google Scholar 

  70. Labat, J.: Ann. Chim. (Paris) 9, 399 (1964)

    Google Scholar 

  71. Fleischmann, M., Korinek, K., Pletcher, D.: J. Electroanal. Chem. 31, 39 (1971)

    Article  Google Scholar 

  72. Fleischmann, M., Korinek, K., Pletcher, D.: J. Electroanal. Chem. 33, 478 (1971)

    Article  Google Scholar 

  73. Robertson, P. M.: J. Electroanal. Chem. 111, 97 (1980)

    Google Scholar 

  74. Vertes, G., Nagy, F.: Acta Chim. Hung. 74, 405 (1972); Chem. Abstr. 78, 57403 (1973)

    Google Scholar 

  75. Vertes, G., Horanyi, G., Nagy, F.: Acta Chim. Hung. 69, 341 (1971); Chem. Abstr. 75, 104502 (1971)

    Google Scholar 

  76. Vertes, G., Horanyi, G.: J. Electroanal. Chem. 52, 47 (1974)

    Article  Google Scholar 

  77. Schäfer, H. J., Mester, Z.: unpublished

    Google Scholar 

  78. Amjad, M., Pletcher, D., Smith, C.: J. Electrochem. Soc. 124, 203 (1977)

    Google Scholar 

  79. Kaulen, H., Schäfer, H. J.: unpublished

    Google Scholar 

  80. Vertes, G., Horanyi, G., Nagy, F.: Kem. Foly 78, 348 (1972); Chem. Abstr. 77, 82870 (1972)

    Google Scholar 

  81. Konaka, R., Terabe, S., Kuruma, K.: J. Org. Chem. 34, 1334 (1969)

    Article  Google Scholar 

  82. Lit. 1a), pp. 851

    Google Scholar 

  83. Steckhan, E.: Angew. Chem. 98, 681 (1986); Angew. Chem. Int. Ed. Engl. 25, 693 (1986)

    Google Scholar 

  84. Evans, D. H., van Effen, R. M.: J. Electroanal. Chem. 103, 383 (1979); 107, 405 (1980)

    Article  Google Scholar 

  85. Vertes, G., Nagy, F.: Acta Chim. Acad. Sci. Hung. 71, 333 (1972)

    Google Scholar 

  86. Morrison, T. N., Schick, K. G., Huber, C. O.: Anal. Chim. Acta 120, 75 (1980); Chem. Abstr. 94, 24538y (1980)

    Article  Google Scholar 

  87. Hui, B. S., Huber, C. O.: Anal. Chim. Acta 134, 211 (1982); Chem. Abstr. 96, 135041s (1982)

    Article  Google Scholar 

  88. Schneider, R.: Diplom-Thesis, Münster 1987

    Google Scholar 

  89. Snoble, K. A. J.: US. Pat., Dow Chem. Co., Chem. Abstr. 100, 128881 (1984)

    Google Scholar 

  90. Feldhues, U.: Ph. D. Thesis, Münster 1984

    Google Scholar 

  91. Stutts, K. J.: US. Pat., Chem. Abstr. 101, 119442q (1984)

    Google Scholar 

  92. Stutts, K. J., Snoble, K. A. J.: US. Pat., Chem. Abstr. 102, 86474s (1985)

    Google Scholar 

  93. Campbell, K. D., Gulbenkian, A. H., Edamura, F. Y., Kyriacou, D.: US. Pat., Chem. Abstr. 102, 122076z (1985)

    Google Scholar 

  94. Blickle, P.: Pat., Chem. Abstr. 105, 87527 (1986)

    Google Scholar 

  95. Kaulen, H.: Ph. D. Thesis, Münster 1981

    Google Scholar 

  96. Court, D., Platcher, D.: Abstr. Nr. 334, Spring Meeting of the Electrochemistry Soc. 1984, Cincinnati, Ohio

    Google Scholar 

  97. Corey, E. J., Schmidt, G.: Tetrahedron Lett. 399 (1979)

    Google Scholar 

  98. Ruholl, H., Schäfer, H. J.: unpublished

    Google Scholar 

  99. Fried, J., Edwards, J. A. (eds.): Organic Reactions in Steroid Chemistry, Vol. 1, pp. 222–264, van Nostrand, New York (1972)

    Google Scholar 

  100. Djerassi, C. (ed.): Steroid Reactions, pp. 91–134, Holden Day, San Francisco 1963

    Google Scholar 

  101. McKillop, A., Young, D. W.: Synthesis 401 (1979)

    Google Scholar 

  102. Heyns, K., Blazejewicz, L.: Tetrahedron 9, 67 (1960)

    Article  Google Scholar 

  103. Heyns, K., Paulsen, H., Rüdiger, G., Weyer, J.: Fortschr. Chem. Forsch. 11, 285 (1969)

    Google Scholar 

  104. Sneeden, R. P. A., Turner, R. B.: J. Am. Chem. Soc. 77, 190 (1955)

    Article  Google Scholar 

  105. Beckmann, S., Geiger, H.: Chem. Ber. 94, 48 (1961)

    Google Scholar 

  106. Alder, K., Hartmann, R., Roth, W.: Chem. Ber. 93, 2271 (1960)

    Google Scholar 

  107. Gopal, H., Adams, T., Moriarty, R. M.: Tetrahedron 28, 4259 (1972)

    Article  Google Scholar 

  108. Moriarty, R. M., Chien, C. C., Adams, T. B.: J. Org. Chem 44, 2210 (1979)

    Article  Google Scholar 

  109. Ruholl, H., Schäfer, H. J.: Synthesis, 1987, 408

    Google Scholar 

  110. Balachandran, K. S., Bhatnagar, I., George, M. V.: J. Org. Chem. 33, 3891 (1968)

    Article  Google Scholar 

  111. Feldhues, U.: Diplom-Thesis, Münster 1981

    Google Scholar 

  112. Robertson, P. M., Schwager, F., Ibl, N.: Electrochim. Acta 18, 923 (1973)

    Article  Google Scholar 

  113. Feldhues, U., Schäfer, H. J.: Synthesis 145 (1982)

    Google Scholar 

  114. Fleischmann, M., Korinek, K., Pletcher, D.: J. Electroanal. Chem. 31, 39 (1971)

    Article  Google Scholar 

  115. Stojiljkovic, A., Andrejevic, V., Mihailovic, M.: Tetrahedron 23, 721 (1967)

    Article  Google Scholar 

  116. Mulina, T. E., Avrutskaya, I. A., Fioshin, M. Y.: Elektrokhimiya 10, 481 (1974); Chem. Abstr. 81, 32499h (1974)

    Google Scholar 

  117. Ruholl, H.: Diplom-Thesis, Münster 1984

    Google Scholar 

  118. Rawalay, S. S., Shechter, H.: J. Org. Chem. 32, 3129 (1967)

    Article  Google Scholar 

  119. Corey, E. J., Achiwa, K.: J. Am. Chem. Soc. 91, 1429 (1969)

    Article  Google Scholar 

  120. Kunugi, A., Shimazu, T., Izumi, I., Nagawa, S.: Num. Fac. Eng., Osaka City Univ. 1976, 101; Chem. Abstr. 88, 90008 (1978)

    Google Scholar 

  121. Lacan, M., Rogic, V.: Electrochim. Acta 28, 199 (1983)

    Article  Google Scholar 

  122. Stephens, F. F., Bower, J. D.: J. Chem. Soc. 1949, 2971; ibid. 1950, 1722

    Google Scholar 

  123. Yoshifuji, M., Nagase, R., Kawashima, T., Inamoto, N.: Heterocycles 10, 57 (1978)

    Google Scholar 

  124. Nakagawa, K., Onoue, H., Sugita, J.: Chem. Pharm. Bull. 12, 1135 (1964)

    PubMed  Google Scholar 

  125. Evans, D. L., Minster, D. K., Jordis, U., Hecht, S. M., Mazzu, A. L., Jr., Meyers, A. I.: J. Org. Chem. 44, 497 (1979)

    Article  Google Scholar 

  126. Fleischmann, M., Korinek, K., Pletcher, D.: J. Electroanal. Chem. 34, 499 (1972); Chem. Abstr. 76, 135041 (1972)

    Article  Google Scholar 

  127. Jap. Pat., Chem. Abstr. 100, 179722v, 17923w, 179724x (1984)

    Google Scholar 

  128. Ohta, H., Tokumaru, K.: Bull. Chem. Soc. Jpn. 44, 3478 (1971)

    Google Scholar 

  129. Back, T. G., Kerr, R. G.: Can. J. Chem. 60, 2711 (1982)

    Google Scholar 

  130. Bhatnagar, I., George, M. V.: J. Org. Chem. 33, 2407 (1968)

    Article  Google Scholar 

  131. Dervan, P. B., Squillacote, M. E., Lahti, P. M., Sylwester, A. P., Roberts, J. D.: J. Am. Chem. Soc. 103, 1120 (1981)

    Article  Google Scholar 

  132. Bradley, G. F., Evans, W. B. L., Stevens, J. D. R.: J. Chem. Soc. Perkin Trans. II, 1214 (1977)

    Google Scholar 

  133. Balachandran, K. S., George, M. V.: Tetrahedron 29, 2119 (1973)

    Article  Google Scholar 

  134. Nakagawa, K., Onoue, H., Minami, K.: Chem. Commun. 1966, 730

    Google Scholar 

  135. Stecher, K. H.: in Houben-Weyl „Methoden der organischen Chemie“ Bd. 4/1b, Stuttgart 1975, pp. 843

    Google Scholar 

  136. Tsuji, J., Hayakawa, S., Takayanagi, H.: Chem. Lett. 1975, 437

    Google Scholar 

  137. Tsuji, J., Kezuka, H., Toshida, Y., Takayanagi, H., Yamamoto, K.: Tetrahedron 39, 3279 (1983)

    Article  Google Scholar 

  138. Cope, A. C., Smith, C. S., Cotter, R. J.: Organic Synthesis, Coll. Col. IV, New York 1963, p. 377

    Google Scholar 

  139. Schmidt, W.: Ph. D.-Thesis, Münster 1982

    Google Scholar 

  140. Mukaiyama, T., Matsueda, R., Suzuki, M.: Tetrahedron Lett. 1901 (1970)

    Google Scholar 

  141. Lloyd, K., Young, G. T.: J. Chem. Soc. 1971, 2890

    Google Scholar 

  142. Corey, E. J., Ulrich, P., Fitzpatrick, J. M.: J. Am. Chem. Soc. 98, 222 (1976)

    Article  Google Scholar 

  143. Gerlach, H., Künzler, P.: Helv. Chim. Acta 63, 2312 (1980)

    Article  Google Scholar 

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    Hans-Jürgen Schäfer

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Schäfer, HJ. (1987). Oxidation of organic compounds at the nickel hydroxide electrode. In: Steckhan, E. (eds) Electrochemistry I. Topics in Current Chemistry, vol 142. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-17871-6_13

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