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Abstract

Oxidations with manganese (III) acetate can be broadly divided into two classes:

  1. 1.

    Direct inner- or outer-sphere one-electron oxidation of the substrate after formation of an inner- or outer-sphere substrate-Mn(III) complex. Often subsequent oxidation of an intermediate radical is product determining. Numerous examples can be found in oxidations of alcohols, amino- and thio-compounds, carboxylic acids, and certain aromatics.

  2. 2.

    Indirect oxidation of the substrate after formation of an intermediate adduct free radical from interaction of manganese (III) acetate and an enolizable compound and subsequent addition or substitution of this radical to the substrate. Most examples here refer to aromatic substitution and oxidative addition of enolizable compounds to unsaturated systems.

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References

  1. W. J. de Klein, Thesis, Leiden (1967).

    Google Scholar 

  2. O. T. Christensen, J. Prakt. Chem. 281 (1883).

    Google Scholar 

  3. O. T. Christensen, Z. Anorg. Allgem. Chem. 27, 323 (1901).

    Google Scholar 

  4. E. Späth, Monatsh. Chem. 33, 242 (1912).

    Google Scholar 

  5. A. Chretien and G. Varga, Bull. Soc. Chim. France 3, 2385 (1936).

    CAS  Google Scholar 

  6. R. W. de Korte, Thesis, Leiden (1964).

    Google Scholar 

  7. L. W. Hessel, Thesis, Leiden (1968).

    Google Scholar 

  8. J. M. Anderson and J. K. Kochi, J. Am. Chem. Soc. 92, 2450 (1970).

    CAS  Google Scholar 

  9. M. Sem, Z. Elektrochem. 21, 426 (1915).

    CAS  Google Scholar 

  10. H. Copaux, C. R. Acad. Sci. 136, 373 (1903).

    Google Scholar 

  11. S. A. Butter, U.S. Patent No. 3, 647. 835 (1969).

    Google Scholar 

  12. J. M. Vaerman and J. N. M. Bertrand, German Patent No. 2, 124, 876 (1972).

    Google Scholar 

  13. L. W. Hessel and C Romers, Reel. Trav. Chim. 88, 545 (1969).

    CAS  Google Scholar 

  14. T. Szymanska-Buzar and J. J. Ziolkowski, Sov. J. Coord. Chem. 2, 897 (1976) [Koord. Khim.2, 1172(1976)].

    Google Scholar 

  15. P. J. Andrulis, M. J. S. Dewar, R. Dietz, and R. L. Hunt, J. Am. Chem. Soc. 88, 5473 (1966).

    CAS  Google Scholar 

  16. R. F. Weinland and G. Fischer, Z. Anorg. Allgem. Chem. 120, 161 (1922).

    Google Scholar 

  17. W. J. de Haas and B. H. Schulz, Physica 6, 481 (1939).

    Google Scholar 

  18. H. D. Hardt and M. Fleischer, Z. Anorg. Allgem. Chem. 357, 113 (1968).

    CAS  Google Scholar 

  19. G. Brauer, Handbuch der Präparativen Anorganischen Chemie, Stuttgart (1962).

    Google Scholar 

  20. J. B. Busch Jr. and H. Finkbeiner, J. Am. Chem. Soc. 90, 5903 (1968).

    Google Scholar 

  21. E. I. Heiba, R. M. Dessau, and W. J. Koehl. J. Am. Chem. Soc. 90, 5905 (1968).

    CAS  Google Scholar 

  22. W. J. de Klein, Reel. Trav. Chim. Pays-Bos 94, 48 (1975); U.S. Patent No. 4,014,910 (1977).

    Google Scholar 

  23. E. L. Heiba, R. M. Dessau, and P. G. Rodewald, J. Am. Chem. Soc. 96, 7977 (1974).

    CAS  Google Scholar 

  24. W. J. de Klein, Reel. Trav. Chim. Pays-Bas 96, 22 1977.

    Google Scholar 

  25. F. J. McQuillin and M. Wood, J. Chem. Soc. Chem. Commun., 65 (1976).

    Google Scholar 

  26. G. L. Nikishin, M. G. Vinogradov, and T. M. Fedorova, J. Chem. Soc. Chem. Commun. 18, 693 (1973).

    Google Scholar 

  27. W. J. de Klein, Reel. Trav. Chim. Pays-Bas 94, 151 (1975).

    Google Scholar 

  28. M. G. Miles, British Patent No. 1,303,831 (1970).

    Google Scholar 

  29. R. B. Mane and G. S. Krishna Rao, J. Chem. Soc. Perkin Trans1, 1235 (1975).

    Google Scholar 

  30. G. Schlewer, J. L. Stampf, and C. Benezza, Can. J. Biochem. 56, 153 (1978).

    CAS  Google Scholar 

  31. K. Witkiewicz and Z. Chabudzinski, Rocz. Chem. 51, 2155 (1977).

    CAS  Google Scholar 

  32. A. Mee, German Patent No. 2,016,820 (1969).

    Google Scholar 

  33. H. L. Finkbeiner and J. B. Bush Jr., German Patent No. 1,933,683 (1968).

    Google Scholar 

  34. H. L. Finkbeiner and J. B. Bush Jr., German Patent No. 1,933,682 (1968).

    Google Scholar 

  35. M. Okano, Bull. Chem. Soc. Jpn. 49, 1041 (1976).

    CAS  Google Scholar 

  36. H. L. Finkbeiner and J. B. Bush Jr., Discuss. Far. Soc. 46, 150 (1968).

    Google Scholar 

  37. M. Okano, Chem. Lett., 165 (1973).

    Google Scholar 

  38. E. I. Heiba and R. M. Dessau, U.S. Patent No. 3,758,513.

    Google Scholar 

  39. M. Okano, J. Sci. Hiroshima Univ. Ser. A: Phys. Chem. 40, 169 (1976).

    CAS  Google Scholar 

  40. R. C Cambie, S. H. Leong, B. D. Palmer, and A. F. Preston, Aust. J. Chem. 33, 155 (1980).

    CAS  Google Scholar 

  41. A. Kasahara, T. Izumi, A. Suzuki, and T. Takeda, Bull. Chem. Soc. Jpn. 49, 3711 (1976).

    CAS  Google Scholar 

  42. A. Sugie, H. Shimomura, J. Katsube, and H. Yamamoto, Tetrahedron Lett., 2759 (1977).

    Google Scholar 

  43. K. Yanagi and T. Nishiyama, Nippon Kagaku Kaishi, 404 (1978).

    Google Scholar 

  44. M. Okano and T. Aratani, J. Sci. Hiroshima Univ. Ser. A-2 33, 71 (1969).

    Google Scholar 

  45. M. Okano and T. Aratani, Mem. Fac. Gen. Ed. Hiroshima Univ. Ill 1, 31 (1967).

    Google Scholar 

  46. M. E. Nambudiry and G. S. Krishna, Indian J. Chem. 13, 633 (1975).

    CAS  Google Scholar 

  47. K. Witkiewicz and Z. Chabudzinski. Rocz. Chem. 50, 1545 (1976).

    CAS  Google Scholar 

  48. K. Witkiewicz and Z. Chabudzinski, Rocz. Chem. 51, 475 (1977).

    CAS  Google Scholar 

  49. K. Witkiewicz and Z. Chabudzinski, Rocz. Chem. 51, 825 (1977).

    CAS  Google Scholar 

  50. K. Witkiewicz and Z. Chabudzinski, Bull. Acad. Pol. Sci., Ser. Sci. Chim. 26, 753 (1978).

    CAS  Google Scholar 

  51. C Walling and E. S. Huyser, Org. Reactions 13, 91 (1964).

    Google Scholar 

  52. C. Walling, Free Radicals in Solution, Wiley, New York, 1957, p. 273.

    Google Scholar 

  53. M. Hatada, J. Takerzaki, and K. Hirota, Bull. Chem. Soc. Jpn. 37, 166 (1964).

    CAS  Google Scholar 

  54. M. G. Vinogradov, R. V. Kereselidze, G. G. Gachechiladze, and G. I. Nikishin, Izv. Akad. Nauk SSSR Ser. Khim., 322 (1969).

    Google Scholar 

  55. M. G. Vinogradov, S. P. Verenchikov, and G. I. Nikishin, Izv. Akad. Nauk SSSR Ser. Khim., 982 (1972).

    Google Scholar 

  56. M. G. Vinogradov, G. P. Il′ina, A. V. Ignatenko, and G. I. Nikishin, Zh. Org. Khim. 8, 539 (1972).

    Google Scholar 

  57. G. I. Nikishin, M. G. Vinogradov, and S. P. Verenchikov, Izv. Akad. Nauk SSSR Ser. Khimi, 1835 (1969).

    Google Scholar 

  58. G. I. Nikishin, M. G. Vinogradov, S. P. Verenchikov, I. N. Kostyukov and R. V. Kereselidze, Zh.Org. Khim.Z 8, 539 (1972).

    CAS  Google Scholar 

  59. G. I. Nikishin, M. G. Vinogradov, and G. P. Il′ina, Synthesis,376 (1972).

    Google Scholar 

  60. G. I. Nikishin, M. G. Vinogradov, and G. P. Il′ina, Zh. Org. Khim. 8, 1401 (1972).

    CAS  Google Scholar 

  61. M. G. Vinogradov, G. P. Il’ina, and G. I. Nikishin, Zh. Org. Khim. 10, 1153 (1974).

    CAS  Google Scholar 

  62. M. Ya. Khorlina and R. Kh. Freidlina, Izv. Akad. Nauk SSSR, Ser. Khim., 933 (1967).

    Google Scholar 

  63. British Patent No. 715.028; Chem. Ahstr. 49. 15948 (1955).

    Google Scholar 

  64. E. I. Heiba and R. M. Dessau, U.S. Patent No. 4,011,239; German Patent No. 1,936,261.

    Google Scholar 

  65. E. I. Heiba and R. M. Dessau. J. Am. Chem. Soc. 93, 524 (1971).

    CAS  Google Scholar 

  66. M. G. Vinogradov, S. P. Verenchikov, and G. I. Nikishin, Zh. Org. Khim. 8, 2467 (1972).

    CAS  Google Scholar 

  67. M. G. Vinogradov, T. M. Fedorova, and G. I. Nikishin, Izv. Akad. Nauk. SSSR Ser. Khim, 2384 (1974).

    Google Scholar 

  68. M. G. Vinogradov, S. P. Verenchikov, T. M. Fedorova, and G. I. Nikishin, Zh. Org. Khim. 11, 947 (1975).

    CAS  Google Scholar 

  69. M. G. Vinogradov, T. M. Fedorova, G. I. Nikishin, Zh. Org. Khim. 11, 1380 (1975).

    CAS  Google Scholar 

  70. R. De Simone and E. Platone, German Patent No. 2,741, 632.

    Google Scholar 

  71. M. G. Vinogradov, T. M. Fedorova, and G. I. Nikishin, Zh. Org. Khim. 12, 1175 (1976).

    CAS  Google Scholar 

  72. M. G. Vinogradov, P. A. Direi, and G. I. Nikishin, Zh. Org. Khim. 13, 2498 (1977).

    CAS  Google Scholar 

  73. O. N. Petrenko, M. G. Vinogradov, S. P. Verenchikov, A. Ya. Shteinshneider, A. B. Terentèv, and G. I. Nikishin, Zh. Org. Khim. 14, 1386 (1978).

    CAS  Google Scholar 

  74. M. G. Vinogradov, O. N. Petrenko, S. P. Verenchikov, A. B. Terentèv, and G. I. Nikishin, Izv. Akad. Nauk. SSSR, Ser. Khim., 1420 (1979).

    Google Scholar 

  75. F. J. McQuillin and M. Wood, J. Chem. Res., S61 (1977).

    Google Scholar 

  76. M. Okano and T. Aratani, Bull. Chem. Soc. Jpn. 49, 2811 (1976).

    CAS  Google Scholar 

  77. R. M. Dessau and E. I. Heiba, J. Org. Chem. 39, 3457 (1974).

    CAS  Google Scholar 

  78. E. I. Heiba and. R. M. Dessau, J. Org. Chem. 39. 3456 (1974).

    CAS  Google Scholar 

  79. K. Ohkata, T. Isako, and T. Hanafusa, Chem. Ind. (London), 274 (1978).

    Google Scholar 

  80. M. G. Vinogradov, O. N. Petrenko, S. P. Verenchikov, and G. I. Nikishin, Izv. Akad. Nauk. SSSR, Ser. Khim., 1916 (1979).

    Google Scholar 

  81. E. I. Heiba and R. M. Dessau, J. Am. Chem. Soc. 94, 2888 (1972).

    CAS  Google Scholar 

  82. D. S. Brown, H. Heaney, S. V. Leij, K. G. Mason, and P. Singh, Tetrahedron Lett. 41, 3937 (1978).

    Google Scholar 

  83. M. Chatzopoulos and J. P. Montheard, C. R. Acad. Sci. Ser. C 284, 133 (1977).

    CAS  Google Scholar 

  84. W. J. de Klein, German Patent No. 2,548,625.

    Google Scholar 

  85. E. Heiba, R. M. Dessau, and W. J. Koehl, J. Am. Chem. Soc. 91, 138 (1969).

    CAS  Google Scholar 

  86. R. E. van der Ploeg, thesis, Leiden (1967).

    Google Scholar 

  87. R. E. van der Ploeg, R. W. de Korte, and E. C. Kooyman. J. Catal. 10, 52 (1968).

    Google Scholar 

  88. K. Kurosawa and H. Harada, Bull. Chem. Soc. Jpn. 52, 2386 (1979).

    CAS  Google Scholar 

  89. M. G. Vinogradov, S. P. Verenchikov, and G. I. Nikishin, Izv. Akad. Nauk SSSR Ser. Khim., 1674 (1972).

    Google Scholar 

  90. M. G. Vinogradov, P. A. Direi, and G. I. Nikishin, Izv. Akad. Nauk SSSR Ser. Khim. 12, 2721 (1976).

    Google Scholar 

  91. M. E. Kurz and R. T. Y. Chen, J. Chem. Soc, Chem. Commun., 968 (1976).

    Google Scholar 

  92. M. E. Kurz and R. T. Chen, J. Org. Chem. 43. 239 (1978).

    CAS  Google Scholar 

  93. A. J. Bellamy, Acta Chem. Scand. Ser. B. B33. 208 (1979).

    CAS  Google Scholar 

  94. S. A. Zonis and Yu. I. Kormlova, Zh. Obshehei Khim. 20. 1252 (1950).

    CAS  Google Scholar 

  95. V. M. Gol’dberg and L. K. Obukhova, Neftekhimiya 7(1), 88 (1967).

    Google Scholar 

  96. N. G. Digurov, N. D. Gravilenko, N. V. Bukharkina, and E. S. Enyukova. Kinet. Katai 19(1), 136 (1978).

    CAS  Google Scholar 

  97. S. G. Nikitina, M. E. Rozenberg, and S. G. Lyubetskii, Vysokomol. Soedin. Ser. B 11(9), 685 (1969); Plast. Massy1970(11), 13; Vysokomol. Soedin. Ser. B14(2), 150 (1972).

    CAS  Google Scholar 

  98. J. M. Bronsdijk, thesis, Leiden (1965).

    Google Scholar 

  99. Tokaaki Aratani and Michael J, S. Dewar, J. Am. Chem. Soc. 88(23), 5479 (1966).

    CAS  Google Scholar 

  100. B. Rindone and C. Scolastico, Tetrahedron Lett.1974(38), 3379.

    Google Scholar 

  101. I. H. Bowen, P. Gupta, M. S. Khan, and J. R. Lewis, J. Chem. Soc, Perkin Trans. 11972(20), 2524.

    Google Scholar 

  102. J. R. Gilmore and J. M. Mellor, J. Chem. Soc. D1970(8), 507.

    Google Scholar 

  103. J. R. Gilmore and J. M. Mellor, Tetrahedron Lett.1971(43), 3977.

    Google Scholar 

  104. T. Shono, K. Yamanoi, T. Matsushika, and K. Shinza, Kogyo Kagaku Zasshi 70(11), 2062 (1967).

    CAS  Google Scholar 

  105. R. van Helden, A. F. Bickel, and E. C. Kooijman, Rec. Trav. Chim. 80, 57 (1961).

    Google Scholar 

  106. K. Kurosawa, Bull. Chem. Soc. Jpn. 42(5), 1456 (1969).

    CAS  Google Scholar 

  107. K. Kurosawa and J. Higuchi, Bull. Chem. Soc. Jpn 45(4), 1132 (1972).

    CAS  Google Scholar 

  108. W. D. Ollis and K. L. Ormand, J. Chem. Soc. C1970, 119.

    Google Scholar 

  109. S. Ueda and K. Kurosawa. Bull. Chem. Soc. Jpn. 50(1), 193 (1977).

    CAS  Google Scholar 

  110. R. Devarajan, P. Elayaperumal, T. Balakrishnan, and M. Santappa, Indian J. Chem., Sec. A 18A(6), 488 (1979).

    CAS  Google Scholar 

  111. K. Oishi and K. Kurosawa, Bull. Chem. Soc. Jpn. 53, 179 (1980).

    CAS  Google Scholar 

  112. G. M. Gorter-Laroy and E. C. Kooijman, J. Catal. 25, 230 (1972).

    Google Scholar 

  113. L. Eberson, J. Am. Chem. Soc. 89, 4669 (1967).

    CAS  Google Scholar 

  114. J. M. Davidson and C. Triggs, J. Chem. Soc. A1968(6), 1331.

    Google Scholar 

  115. P. J. Andruhs and M. J. S. Dewar, J. Am. Chem. Soc. 88(23), 5483 (1966).

    Google Scholar 

  116. S. Uemura, T. Ikeda, S. Tanaka, and M. Okano, J. Chem. Soc. Perkin Trans. I1979(10), 2574.

    Google Scholar 

  117. S. A. Zonis, Sbornik Statci Obshehei Khim. 2, 1091 (1953).

    CAS  Google Scholar 

  118. R. van Helden, A. F. Bickel, and E. C. Kooyman, Rec. Trav. Chim. 80, 1257 (1961).

    CAS  Google Scholar 

  119. A. Onopchenko and J. G. D. Schulz, J. Org. Chem. 37(16), 2564 (1972).

    CAS  Google Scholar 

  120. T. V. Bukharkina, N. D. Gavrilenko, N. G. Digurov, and N. A. Knyazeva, Kinet. Katal. 19(2), 506 (1978).

    CAS  Google Scholar 

  121. P. De Radzitzky and J. Hanotier, French Patent No. 2, 030,543.

    Google Scholar 

  122. J. Hanotier, M. Hanotier-Bridoux, and P. Dc Radzitzky, J. Chem. Soc. Perkin Trans. II1973(4), 381.

    Google Scholar 

  123. E. Baciocchi, L. Mandolini, and C. Rol, J. Org. Chem. 45, 3906 (1980).

    CAS  Google Scholar 

  124. K. Nijberg and L. G. Wistrand. Chem. Ser. 6(5), 234 (1974).

    Google Scholar 

  125. S. Tanaka, S. Uemura, and M. Okano. J. Chem. Soc. Perkin Trans. I1978(5), 431.

    Google Scholar 

  126. M. Okano and T. Aratani, J. Sci. Hiroshima Univ., Ser. a7/31(2), 69 (1967).

    Google Scholar 

  127. M. Okano and T. Aratani, Mem. Fac. Gen. Ed. Hiroshima Univ. Ill 1, 31 (1967).

    Google Scholar 

  128. M. Okano, Chem. Ind.London; 1972(10), 423.

    Google Scholar 

  129. J. R. Gilmore and J. M. Mellor, J. Chem. Soc. C1971(12), 2355.

    Google Scholar 

  130. A. Kasahara, R. Saito. and T. Izumi. Bull. Chem. Soc. Jpn. 46, 2610 (1973).

    Google Scholar 

  131. Z. V. Todres, M. G. Vinogradov, D. Kursanov and G. I. Nikishin, Tezisy Dokl. Vses. Soveshch. Kompleksam. Perenosom Zaryada lon-Radikal’nym Solyam, 3rd 1975. C.A. 87, 38514e (1975).

    Google Scholar 

  132. M. G. Vinogradov, Z. V. Todres, G. P. IHna, A. Rutavicius, D. N. Kursanov, and G. I. Nikishin, Izv. Akad. Nauk. SSSR, Ser. Khim.1976(6), 1331.

    Google Scholar 

  133. H. Sekizaki, M. Ito, and S. Inoue, Bull. Chem. Soc. Jpn. 51(12), 3663 (1978).

    CAS  Google Scholar 

  134. J. M. Roqué, An. Quim. 66(6), 607 (1970).

    Google Scholar 

  135. G. J. Williams and N. R. Hunter, Can. J. Chem. 54(24), 3830 (1976).

    CAS  Google Scholar 

  136. H. L. Finkbeiner and J. B. Bush, U.S. Patent No. 3,535,372.

    Google Scholar 

  137. H. L. Finkbeiner and J. B. Bush, U.S. Patent No. 3,927,077.

    Google Scholar 

  138. A. Onopchenko and J. Schulz, J. Org. Chem. 40(23), 3338 (1975).

    CAS  Google Scholar 

  139. T. Izumi. Y. Satou, Y. Yoshida and A. Kasahara. Bull. Chem. Soc. Jpn. 52(5), 1551 (1979).

    Google Scholar 

  140. M. G. Vinogradov, P. A. Direi, and G. I. Nikishin, Zh. Org. Khim. 12, 527 (1976).

    CAS  Google Scholar 

  141. W. J. de Klein, unpublished work.

    Google Scholar 

  142. E. S. Gould, Mechanism and Structure in Organic Chemistry, Holt. Rinehart and Winston, New York. 1962, p. 383.

    Google Scholar 

  143. M. G. Vinogradov, P. A. Direi, and G. I. Nikishin. Zh. Org. Khim. 14, 2043 (1978).

    CAS  Google Scholar 

  144. H. A. P. de Jongh, C. R. H. I. de Jonge, H. J. M. Sinnige, W. J. de Klein. W. G. B. Huysmans, and W. J. Mijs, J. Org. Chem. 37. 1960 (1972).

    Google Scholar 

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de Klein, W.J. (1986). Reactions with Manganese (III) Acetate. In: Mijs, W.J., de Jonge, C.R.H.I. (eds) Organic Syntheses by Oxidation with Metal Compounds. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2109-5_4

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