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Oxidation of Alcohols

  • Chapter
Chromium Oxidations in Organic Chemistry

Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 19))

Abstract

The oxidation of alcohols constitutes the synthetically most important application of chromium(VI) oxidation. The matter has been largely divided into 4 sections: The first section includes acid catalysed oxidations with chromium trioxide and chromic acid in a variety of solvents including water, acetic acid, acetone (Jones’ reagent), dimethylsulphoxide, and dimethylformamide. A second section deals with oxidations promoted by a family of chromium(VI) reagents obtained from chromium trioxide, chromic acid, and halochromic acids with heterocyclic bases. Important members of this class are the chromium trioxide-(pyridine)2 complex (Sarett’s reagent) and the pyridinium chlorochromate introduced by E. J. Corey. The third section describes oxidations carried out under neutral or almost neutral conditions. It includes oxidations with di-tert-butyl chromate, chromium trioxide in hexamethylphosphoramide, and with tetrabutylammonium salts of chromic acid under various conditions. A fourth section deals with the recently introduced chromium(VI) reagents supported on various insoluble organic and inorganic matrices. Two smaller sections, which briefly discuss the mechanism of oxidation of alcohols with chromium(VI) and the influence of structure and stereochemistry of the alcohol on the oxidation rate complete the chapter.

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References

  1. Stadeler, I: J. Chem. Soc. 1859 ,329

    Google Scholar 

  2. Beckmann, E.: Liebigs Ann. Chem. 250 ,322 (1889)

    Google Scholar 

  3. Kiliani, H.: Chem. Ber. 46 ,667 (1913)

    CAS  Google Scholar 

  4. Wiberg, K. B., Mill, T.: J. Am. Chem. Soc. 80 ,3019 (1958)

    CAS  Google Scholar 

  5. Mosher, W. A., Preiss, D. M.: ibid. 75 ,5605 (1953)

    CAS  Google Scholar 

  6. Hurd, C. D., Meinert, R. N.: Org. Synth. Coll. 2 ,541 (1943)

    Google Scholar 

  7. Demiankow, N. J., Fortunatow, K.: Chem. Ber. 40 ,4937 (1907)

    Google Scholar 

  8. Sauer, J. C: Org. Synth. Coll. 4 ,813 (1963)

    Google Scholar 

  9. Adams, C. E., Williams, R. J.: J. Am. Chem. Soc. 43 ,2420 (1921)

    CAS  Google Scholar 

  10. Fossek, W.: Monatsh. 2 ,614 (1881)

    Google Scholar 

  11. Fossek, W.: ibid. 4 ,660 (1883)

    Google Scholar 

  12. Kuhn, R., Grundmann, C: Chem. Ber. 70 ,1894 (1937)

    Google Scholar 

  13. Badin, E. G., Pacsu, E.: J. Am. Chem. Soc. 67 ,1352 (1945)

    CAS  Google Scholar 

  14. Hurd, C. D., Abernethy, J. L.: ibid. 63 ,1966 (1941)

    CAS  Google Scholar 

  15. Henne, A. L., Penney, R. L., Alm, R. M.: ibid. 72 ,3370 (1950)

    CAS  Google Scholar 

  16. Delaby, R., Quillot-Allegre, S.: Bull. Soc. Chim. Fr. 1933 ,301

    Google Scholar 

  17. Martin, C. J., Schepartz, A. I., Daubert, B. F.: J. Am. Chem. Soc. 70 ,2601 (1948)

    CAS  Google Scholar 

  18. Jacobson, M.: ibid. 72 ,1489 (1950)

    CAS  Google Scholar 

  19. Stoll, M., Commarmont, A.: Helv. Chim. Acta 32 ,1355 (1949)

    Google Scholar 

  20. West, B. L.: J. Am. Chem. Soc. 42 ,1656 (1920)

    CAS  Google Scholar 

  21. Gindraux, L.: Helv. Chim. Acta 12 ,921 (1929)

    CAS  Google Scholar 

  22. Robertson, G. R.: Org. Synth. Coll. 1 ,138 (1944)

    Google Scholar 

  23. Griszkiewicz-Trochimowski, E.: Rec. Trav. Chim. 66 ,430 (1946)

    Google Scholar 

  24. Marckwald, W.: Chem. Ber. 37 ,1038 (1904)

    CAS  Google Scholar 

  25. Nickels, J. E., Heintzelman, W.: J. Org. Chem. 15 ,1142 (1950)

    CAS  Google Scholar 

  26. Yohe, C. R., Louder, H. U., Smith, G. A.: J. Chem. Ed. 10 ,374 (1933)

    CAS  Google Scholar 

  27. Grignard, V., Fluchaire, M.: Ann. Chim. (Paris) 9, 5 (1928)

    CAS  Google Scholar 

  28. Sherrill, M. L.: J. Am. Chem. Soc. 52 ,1982 (1930)

    CAS  Google Scholar 

  29. Mann, F. G., Porter, J. W. G.: J. Chem. Soc. 1944 ,456

    Google Scholar 

  30. Wagner, R. B., Moore, J. A.: J. Am. Chem. Soc. 72 ,974 (1950)

    CAS  Google Scholar 

  31. Grédy, B.: Ann. Chim. (Paris) 4 ,22 (1935)

    Google Scholar 

  32. Osterberg, A. E., Kendall, E. C: J. Am. Chem. Soc. 42 ,2616 (1920)

    CAS  Google Scholar 

  33. Warnhoff, E. W., Martin, D. G., Johnson, W. S.: Org. Synth. 37 ,8 (1957)

    CAS  Google Scholar 

  34. Ungnade, H. E., McLaren, A. D.: J. Org. Chem. 10 ,29 (1945)

    CAS  Google Scholar 

  35. Adkins, H., Hager, G. F.: J. Am. Chem. Soc. 71 ,2965 (1949)

    CAS  Google Scholar 

  36. Huber, W. F., Rewoll, M., Rossow, A. G., Mowry, D. T.: ibid. 68 ,1109 (1946)

    CAS  Google Scholar 

  37. Conant, J. B., Quayle, O. R.: Org. Synth. Coll. 1 ,211 (1941)

    Google Scholar 

  38. Sandborn, L. T.: ibid. Vol. 1, 340 (1941)

    Google Scholar 

  39. Zelinsky, N., Gutt, J.: Chem. Ber. 39 ,3050 (1906)

    Google Scholar 

  40. Sheehan,Z. C., Young, R. L., Cruickshank, P. A.:Z. Am. Cπem. Soc. 82 ,6147 (1960)

    CAS  Google Scholar 

  41. Newman, M. S., Arkell, A., Fukunaga, T.: ibid. 82 ,2498 (1960)

    CAS  Google Scholar 

  42. Pattison, F. L. M., Stothers, J. B., Woolford, R. G.: ibid. 78 ,2255 (1956)

    Google Scholar 

  43. Mann, F. G., Porter, J. W. G.: J. Chem. Soc. 1944 ,456

    Google Scholar 

  44. Price, C. C., Karabinos, J. W.: J. Am. Chem. Soc. 62 ,1159 (1940)

    CAS  Google Scholar 

  45. Mosher, W. A., Langerak, E. O.: ibid. 71 ,286 (1949)

    CAS  Google Scholar 

  46. Whitmore, F. C, Lewis, C. E.: ibid. 64 ,2964 (1942)

    CAS  Google Scholar 

  47. Shunk, C. H., Wilds, A. L.: ibid. 71 ,3946 (1949)

    CAS  Google Scholar 

  48. Lock, G., Schreckeneder, R.: Chem. Ber. 72 ,516 (1939)

    Google Scholar 

  49. Neidig, H. A., Funk, D. L., Uhrich, R., Baker, R., Kreiser, W.: J. Am. Chem. Soc. 72 ,4617 (1950)

    CAS  Google Scholar 

  50. Fieser, L. F., Cason, J.: ibid. 62 ,432 (1940)

    CAS  Google Scholar 

  51. Hanaya, K., Awano, S., Kudo, H.: Bull. Soc. Chim. Jap. 57, 342 (1978)

    Google Scholar 

  52. Rocek, J., Westheimer, F. H., Eschenmoser, A., Moldovanyi, L., Schreiber, J.: Helv. Chim. Acta 45 ,2554 (1962)

    CAS  Google Scholar 

  53. Schreiber, J., Eschenmoser, A.: Helv. Chim. Acta 38 ,1529 (1955)

    CAS  Google Scholar 

  54. Ellis, B., Petrow, V.: J. Chem. Soc. (1939), 1078

    Google Scholar 

  55. Gallagher, T. F., Long, W. P.: J. Biol. Chem. 147 ,131 (1943)

    CAS  Google Scholar 

  56. Davis, ML, Petrow, V.: J. Chem. Soc. (1949) 2536

    Google Scholar 

  57. Neher, R., Desaulles, P., Vischer, E., Wieland, P., Wettstein, A.: Helv. Chim. Acta 41 ,1667 (1958)

    CAS  Google Scholar 

  58. Heusler, K., Kalvoda, J., Meystre, C., Wieland, P., Anner, G., Wettstein, A., Cainelli, G., Arigoni, D., Jeger, O.: ibid. 44 ,502 (1961)

    CAS  Google Scholar 

  59. Wieland, H., Dane, E.: Z. Physiol. Chem. 272, 41 (1932)

    Google Scholar 

  60. Anatol, J., Medète, A.: Synthesis 1977, 538

    Google Scholar 

  61. Hampton, J., Leo, A., Westheimer, F. H.: J. Am. Chem. Soc. 78 ,306 (1956)

    CAS  Google Scholar 

  62. Wiberg, K. B., Mukherjee, S. K.: ibid. 96 ,6647 (1974)

    CAS  Google Scholar 

  63. Rocek, J., Radkowsky, A. E.: ibid. 95 ,7123 (1973)

    CAS  Google Scholar 

  64. Rocek, J., Martinez, A. M., Cushmac, G. E.: ibid. 95 ,5425 (1973)

    CAS  Google Scholar 

  65. Hasan, F., Rocek, J.: ibid. 96 ,534 (1974)

    CAS  Google Scholar 

  66. Corey, E. J., Arnola, Z., Hutton, J.: Tetrahedron Lett. 1970, 307

    Google Scholar 

  67. Cawley, J. J., Spaziano, V. T.: ibid. 1973 ,4719

    Google Scholar 

  68. Rocek, J., Westheimer, F. H.: J. Am. Chem. Soc. 84 ,2241 (1962)

    CAS  Google Scholar 

  69. Walker, B. H.: J. Org. Chem. 32 ,1098 (1967)

    CAS  Google Scholar 

  70. Bowers, A., Halsall, T. G., Jones, E. R. H., Lemin, A. J.: J. Chem. Soc. 1953 ,2548

    Google Scholar 

  71. Djerassi, C. D., Hart, P. A., Warawa, E. J.: J. Am. Chem. Soc. 86 ,78 (1964)

    CAS  Google Scholar 

  72. Ireland, R. E., Schiess, P. W.: Tetrahedron Lett. 1960 ,37

    Google Scholar 

  73. Cardillo, G., Contento, M., Sandri, S., Panunzio, M.: J. Chem. Soc. Perkin I 1979 ,1729

    Google Scholar 

  74. Rodin, J. O., Leaffer, M. A., Silverstein, R. M.: J. Org. Chem. 35 ,3152 (1970)

    CAS  Google Scholar 

  75. Kuzuhara, H., Kimura, M., Emoto, S.: J. Carbonhydr. Res. 45 ,245 (1975)

    CAS  Google Scholar 

  76. Nicolaou, K. C., Pavia, M. R., Seitz, S. P.: Tetrahedron Lett. 1979 ,2327

    Google Scholar 

  77. Cama, L., Cristensen, B. G.: ibid. 1980 ,2013

    Google Scholar 

  78. Pelletier, S. W., Chappell, R. L., Prabhakar, S.: J. Am. Chem. Soc. 90 ,2889 (1968)

    CAS  Google Scholar 

  79. Jefferies, P. R., Rosich, R. S., White, D. E., Woods, M. C.: Austr. J. Chem. 15 ,521 (1962)

    CAS  Google Scholar 

  80. Fujita, E., Fujita, T., Shibuya, M., Shingu, T.: Tetrahedron 25 ,2517 (1969)

    CAS  Google Scholar 

  81. Crandall, J. K., Conover, W. W., Komin, J. B.: J. Org. Chem. 40 ,2042 (1975)

    CAS  Google Scholar 

  82. Balsamo, A., Crotti, P., Ferretti, M., Macchia, F.: ibid. 40 ,2870 (1975)

    CAS  Google Scholar 

  83. Arco, M. J., Trammell, M. H., White, J. D.: ibid. 41 2075 (1976)

    CAS  Google Scholar 

  84. Varma, R. K., Koreeda, M., Yagen, B., Nakanishi, K., Caspi, E.: ibid. 40 ,3680 (1975)

    CAS  Google Scholar 

  85. Lin, C. H., Alexander, D. L.: ibid. 47 ,615 (1982)

    CAS  Google Scholar 

  86. Hanessian, S., Frenette, R.: Tetrahedron Lett. 1979 ,3391

    Google Scholar 

  87. Mussatto, M. C., Savoia, D., Trombini, C., Umani Ronchi, A.: J. Org. Chem. 45 ,4002 (1980)

    CAS  Google Scholar 

  88. Harding, K. E., May, L. M., Dick, K. F.: ibid. 40 ,1664 (1975)

    CAS  Google Scholar 

  89. Heilbron, I., Jones, E. R. H., Sondheimer, F.: J. Chem. Soc. 1947, 1586

    Google Scholar 

  90. Heilbron, I., Jones, E. R. H., Sondheimer, F.: ibid. 1948 ,604

    Google Scholar 

  91. Eisenbraun, E. J.: Org. Synth. 45 ,28 (1965)

    CAS  Google Scholar 

  92. Meinwald, J., Crandall, J., Hymans, W. E.: ibid. 45, 11 (1965)

    Google Scholar 

  93. Heathcock, C. H., Badger, R. A., Patterson Jr., J. W.: J. Am. Chem. Soc. 89 ,4133 (1967)

    CAS  Google Scholar 

  94. Marshall, J. A., Snyder, W. R.: J. Org. Chem. 40 ,1656 (1975)

    CAS  Google Scholar 

  95. Herz, W., Poplawski, J., Sharma, R. P.: ibid. 40 ,199 (1975)

    CAS  Google Scholar 

  96. Tanaka, H., Torii, S.: ibid. 40 ,462 (1975)

    CAS  Google Scholar 

  97. Arco, M. J., Trammell, M. H., White, J. D.: ibid. 41 ,2075 (1976)

    CAS  Google Scholar 

  98. Meyer, W. L., Capshew, C. E., Johnson, J. H., Klusener, A. R., Lobo, A. P., McCarty, R. N.: ibid. 42 ,527 (1977)

    CAS  Google Scholar 

  99. Sharpless, K. B., Chong, A. O., Oshima, K.: ibid. 41, 177 (1976)

    CAS  Google Scholar 

  100. Herz, W., Sharma, R. P.: ibid. 41 ,1021 (1976)

    CAS  Google Scholar 

  101. Sih, C. J., Salomon, R. G., Price, P., Peruzzotti, G., Sood, R.: J. Chem. Soc. Chem. Comm. 1972 ,240

    Google Scholar 

  102. Mayor, P. A., Meakins, G. D.: J. Chem. Soc. 1960 ,2792

    Google Scholar 

  103. Kiely, D. E., Benzing-Nguyen, L.: J. Org. Chem. 40 ,2630 (1975)

    CAS  Google Scholar 

  104. McCrae, D. A., Dolby, L.: ibid. 42 ,1607 (1977)

    CAS  Google Scholar 

  105. Ireland, R. E., Bey, P., Cheng, K. F., Czarny, R. J., Moser, J. F., Trust, R. I.: ibid. 40 ,1000 (1975)

    CAS  Google Scholar 

  106. Mehta, G., Pandey, P. N., Ho, T. L.: ibid. 41 ,953 (1976)

    CAS  Google Scholar 

  107. Wenkert, E., Berges, D. A.: J. Am. Chem. Soc. 89 ,2507 (1967)

    CAS  Google Scholar 

  108. Masamune, S.: ibid. 86 ,291 (1964)

    CAS  Google Scholar 

  109. Tochtermann, W., Schafer, D., Rohr, C.: Chem. Ber. 104 ,2923 (1971)

    CAS  Google Scholar 

  110. Billé-Samé, T., Bergmann, E. D.: Bull. Soc. Chim. Fr. 1972 ,4215

    Google Scholar 

  111. Neff, J. R., Nordlander, J. E.: J. Org. Chem. 41 ,2590 (1976)

    CAS  Google Scholar 

  112. Holick, W., Jenny, E. F., Heusler, K.: Tetrahedron Lett. 1973 ,3421

    Google Scholar 

  113. Godleski, S. A., von R. Schleyer, P., Osawa, E., Inamoto, Y., Fujikura, Y.: J. Org. Chem. 41 ,2596 (1976)

    CAS  Google Scholar 

  114. Murray, R. K. Jr., Babiak, K. A., Morgan Jr., T. K.: ibid. 40 ,2463 (1975)

    CAS  Google Scholar 

  115. Daniewski, A. R., Guzewska, M., Koeór, M.: ibid. 40 ,3131 (1975)

    CAS  Google Scholar 

  116. Neeman, ML, Osawa, Y., Mukai, T.: J. Chem. Soc. Perkin I 1972 ,2297

    Google Scholar 

  117. Chorvat, R. J., Pappo, R.: J. Org. Chem. 41 ,2864 (1976)

    CAS  Google Scholar 

  118. Dauben, W. G., Fullerton, D. S.: ibid. 36 ,3277 (1971)

    CAS  Google Scholar 

  119. Van Beven, W., Kohnen, F., Ranade, V. V., Counsell, R. E.: J. Chem. Soc. Chem. Comm. 1978 ,758

    Google Scholar 

  120. Fried, J., Grabowich, P., Sabo, E. F., Dohen, A. I.: Tetrahedron 20 ,2297 (1964)

    CAS  Google Scholar 

  121. Djerassi, C., Engle, R. R., Bowers, A.: J. Org. Chem. 21 ,1547 (1956)

    CAS  Google Scholar 

  122. Bowden, K., Heilbron, I. M., Jones, E. R. H., Weedon, B. C. L.: J. Chem. Soc. 1946 ,39

    Google Scholar 

  123. Glotter, E., Greenfield, S., Lavie, D.: J. Chem. Soc. (C) 1968 ,1646

    Google Scholar 

  124. Burnstein, S. H., Ringold, H. J.: J. Am. Chem. Soc. 89 ,4722 (1967)

    Google Scholar 

  125. Snatzke, G.: Chem. Ber. 94 ,729 (1961)

    CAS  Google Scholar 

  126. Rosenberg, M., Fraher, T. P., Saucy, G.: Helv. Chim. Acta 54 ,2857 (1971)

    Google Scholar 

  127. Rao, Y. S., Filler, R.: J. Org. Chem. 39 ,3304 (1974)

    CAS  Google Scholar 

  128. Ellis, J. E., Dutcher, J. S., Heatcock, C. H.: ibid. 41 ,2670 (1976)

    CAS  Google Scholar 

  129. Deemer, L. F., Lutwak, L., Strong, F. M.: J. Am. Chem. Soc. 70 ,154 (1948)

    CAS  Google Scholar 

  130. Rasmusson, G. H., House, H. O., Zaweski, E. F., De Puy, C. H.: Org. Synth. 42 ,36 (1962)

    CAS  Google Scholar 

  131. Acharya, S. P., Brown, H. C: J. Org. Chem. 35 ,3874 (1970)

    CAS  Google Scholar 

  132. Brown, H. C., Garg, C. P., Liu, K. T.: ibid. 36 ,387 (1971)

    CAS  Google Scholar 

  133. Kuemmerle, Jr., E. W., Rettig, T. A., Stille, J. K.: ibid. 40 ,3665 (1975)

    CAS  Google Scholar 

  134. Wasserman, H. H., Keith, D. D., Nadelson, J.: J. Am. Chem. Soc. 91 ,1264 (1969)

    CAS  Google Scholar 

  135. Landini, D., Montanari, F., Rolla, F.: Synthesis 1979 ,134

    Google Scholar 

  136. Pletcher, D., Tait, S. J. D.: Tetrahedron Lett. 1978 ,1601

    Google Scholar 

  137. Sisler, H. H., Bush, J. D., Accountius, O. E.: J. Am. Chem. Soc. 70 ,3827 (1948)

    CAS  Google Scholar 

  138. Sisler, H. H., Ming, W. C. L., Metter, E., Hurley, F. R.: ibid. 75 ,446 (1953)

    CAS  Google Scholar 

  139. Poos, G. L, Arth, G. E., Beyler, R. E., Sarett, L. H.: ibid. 75 ,422 (1953)

    CAS  Google Scholar 

  140. Bernstein, S., Lenhard, R. H.: ibid. 82 ,3680 (1960)

    CAS  Google Scholar 

  141. Zderic, J. A., Batres, E., Chavez Limon, D., Carpio, H., Lisci, J., Monroy, G., . Necoechea, E., Ringold, H. J.: ibid. 82 ,3404 (1960)

    CAS  Google Scholar 

  142. Bernstein, S., Heller, M., Feldman, L. I., Allen, W. S., Blank, R., Linden, C. E.: ibid. 82 ,3685 (1960)

    CAS  Google Scholar 

  143. Kenney, H. E., Serota, S., Weaver, E. A., Wall, M. E.: ibid. 82 ,3689 (1960)

    Google Scholar 

  144. Mazur, Y., Danieli, N., Sondheimer, F.: ibid. 82 ,5889 (1960)

    CAS  Google Scholar 

  145. Heusler, K., Kalvoda, J., Meystre, C., Wieland, P., Anner, G., Wettstein, A., Cainelli, G., Arigoni, D., Jeger, O.: Helv. Chim. Acta 61 ,502 (1961)

    Google Scholar 

  146. Labler, L., Sorm, F.: Coll. Czech. Chem. Comm. 25 ,2855 (1960)

    CAS  Google Scholar 

  147. Urech, J., Vischer, E., Wettstein, A.: Helv. Chim. Acta 43 ,1077 (1960)

    CAS  Google Scholar 

  148. Ikegami, S., Kamiya, Y., Tamura, S.: Tetrahedron Lett. 1973 ,731

    Google Scholar 

  149. Holum, J. R.: J. Org. Chem. 26 ,4814 (1961)

    CAS  Google Scholar 

  150. Wasserman, H. H., Aubrey, N. E.: J. Am. Chem. Soc. 77 ,590 (1955)

    CAS  Google Scholar 

  151. Cross, B. E.: J. Chem. Soc. 1960 ,3022

    Google Scholar 

  152. Chawla, R. K., McGonigal, W. E.: J. Org. Chem. 39 ,3281 (1974)

    CAS  Google Scholar 

  153. Neff, J. R., Nordlander, J. E.: ibid. 41 ,2590 (1976)

    CAS  Google Scholar 

  154. Gilbert, J. C, Smith, K. R.: ibid. 41 ,3883 (1976)

    CAS  Google Scholar 

  155. Aiyar, V. N., Chang, F. C.: ibid. 42 ,246 (1977)

    CAS  Google Scholar 

  156. Hill, R. K., Joule, J. A., Loeffler, L. J.: J. Am. Chem. Soc. 84,4951 (1962)

    CAS  Google Scholar 

  157. Perry, D. L., Fischer, N. H.: J. Org. Chem. 40 ,3480 (1975)

    CAS  Google Scholar 

  158. Collins, J. C., Hess, W. W., Frank, F. J.: Tetrahedron Lett. 1968 ,3363

    Google Scholar 

  159. Crabbé, P., Cervantes, A., Meana, M. C: J. Chem. Soc. Chem. Comm. 1973 ,119

    Google Scholar 

  160. Fraser-Reid, B., Walker, D. L., Tarn, S. Y. K., Holder, N. L.: Can. J. Chem. 51, 3950(1973)

    CAS  Google Scholar 

  161. Ratcliffe, R. W., Rodehorst, R.: J. Org. Chem. 35 ,4000 (1970)

    Google Scholar 

  162. Sucrow, W., Scopianska, M., Caldeika, P. P.: Chem. Ber. 108 ,1101 (1975)

    CAS  Google Scholar 

  163. Ratcliffe, R. W., Salzmann, T. N., Christensen, B. G.: Tetrahedron Lett. 1980,31

    Google Scholar 

  164. Pelletier, S. W., Lajsic, S., Ohtsuka, Y., Djarmati, Z.: J. Org. Chem. 40 ,1607 (1975)

    CAS  Google Scholar 

  165. Parker, K. A., Iqbal, T.: ibid. 47 ,337 (1982)

    CAS  Google Scholar 

  166. Mori, K., Kuwahara, S.: Tetrahedron 38 ,521 (1982)

    CAS  Google Scholar 

  167. Sundararaman, P., Herz, W.: J. Org. Chem. 42 ,813 (1977)

    CAS  Google Scholar 

  168. Cornforth, R. H., Cornforth, J. W., Popjak, G.: Tetrahedron 18 ,1351 (1962)

    CAS  Google Scholar 

  169. Wuonola, M. A., Woodward, R. B.: J. Am. Chem. Soc. 95 ,5098 (1973)

    CAS  Google Scholar 

  170. Coates, W. M., Corrigan, J. R.: Chem. Ind. 44 ,1594 (1969)

    Google Scholar 

  171. Miller, F. A., Wilkins, C. H.: Anal. Chem. 24 ,1253 (1952)

    CAS  Google Scholar 

  172. Corey, E. J., Schmidt, G.: Tetrahedron Lett. 1979 ,399

    Google Scholar 

  173. Still, W. C, Galynker, I.: J. Am. Chem. Soc. 104 ,1774 (1982)

    CAS  Google Scholar 

  174. Corey, E. J., Suggs, J. W.: Tetrahedron Lett. 1975 ,2647

    Google Scholar 

  175. Corey, E. J., Boger, D. L.: ibid. 1978 ,2461

    Google Scholar 

  176. Antonioletti, R., D’Auria, M., Piancatelli, G., Scettri, A.: ibid. 1981 ,1041

    Google Scholar 

  177. Meinwald, J., Jones, T. H.: J. Am. Chem. Soc. 100 ,1883 (1978)

    CAS  Google Scholar 

  178. Glaros, G.: J. Chem. Ed. 55 ,410 (1978)

    CAS  Google Scholar 

  179. Corey, E. J., Smith, J. G.: J. Am. Chem. Soc. 101 ,1038 (1979)

    CAS  Google Scholar 

  180. Tatsuta, K., Akimoto, K., Kinoshita, M.: ibid. 101 ,6116 (1979)

    CAS  Google Scholar 

  181. Fish, R. H., Broline, B. M.: J. Organomet. Chem. 159 ,255 (1978)

    CAS  Google Scholar 

  182. Lewis, P. H., Middleton, S., Rosser, M. J., Stock, L.E.: Austr. J. Chem. 32 ,1123(1979)

    CAS  Google Scholar 

  183. Bohlmann, F., Otto, W.: Liebigs Ann. Chem. 1982 ,186

    Google Scholar 

  184. Melvin, G., Rickards, R. W.: J. Chem. Soc. Perkin I 1981 ,599

    Google Scholar 

  185. Brown, H. C, Rao, C. G., Kulkarni, S. U.: J. Org. Chem. 44 ,2809 (1979)

    CAS  Google Scholar 

  186. Hollemberg, D. H., Klein, R. S., Fox, J. J.: J. Carbohydr. Res. 67 ,491 (1978)

    Google Scholar 

  187. Herscovici, J., Antonakis, K.: J. Chem. Soc. Chem. Comm. 1980 ,561

    Google Scholar 

  188. Bhattacharjee, M. N., Chaudhuri, M. K., Dasgupta, H. S., Roy, N., Khathing, D. T.: Synthesis 1982 ,588

    Google Scholar 

  189. (a) Johnson, F., Duquette, L. G., Parker, W. L., Nasutavicus, W. A.: J. Org. Chem. 39 ,1434 (1974)

    CAS  Google Scholar 

  190. Groves, J. K.: Chem. Rev. 1, 73 (1972)

    CAS  Google Scholar 

  191. Dauben, W. G., Michno, D. M.: J. Org. Chem. 42 ,682 (1977)

    CAS  Google Scholar 

  192. Wada, E., Okawara, M., Nakai, T.: ibid. 44 ,2952 (1979)

    CAS  Google Scholar 

  193. Corey, E. J., Fleet, G. W. J.: Tetrahedron Lett. 1973 ,4499

    Google Scholar 

  194. Guziec, F. S. Jr., Luzzio, F. A.: Synthesis 1980 ,691

    Google Scholar 

  195. Guziec, F. S. Jr., Luzzio, F. A.: J. Org. Chem. 47 ,1787 (1982)

    CAS  Google Scholar 

  196. Chakraborty, T. K., Chandrasekaran, S.: Tetrahedron Lett. 1980,1583

    Google Scholar 

  197. Chakraborty, T. K., Chandrasekaran, S.: Synth. Comm. 10 ,951 (1980)

    CAS  Google Scholar 

  198. Suga, T., Kihara, K., Matsura, T.: Bull. Chem. Soc. Japan 38 ,893 (1965)

    CAS  Google Scholar 

  199. Suga, T., Kihara, K., Matsura, T.: ibid. 38 ,1141 (1965)

    CAS  Google Scholar 

  200. Suga, T., Matsuura, T.: ibid. 38 ,1503 (1965)

    CAS  Google Scholar 

  201. Sharpless, K. B., Akashi, K.: J. Am. Chem. Soc. 97 ,5927 (1975)

    CAS  Google Scholar 

  202. Beugelmans, R., Le Goff, M. T.: Bull. Soc. Chim. Fr. 1969 ,335

    Google Scholar 

  203. Cardillo, G., Orena, M., Sandri, S.: Synthesis 1976 ,394

    Google Scholar 

  204. Savona, G., Piozzi, F., Marino, M. L.: Gazz. Chim. It. 107 ,511 (1977)

    CAS  Google Scholar 

  205. Yoshii, E., Oribe, T., Tumura, K., Koizumi, T.: J. Org. Chem. 43 ,3946 (1978)

    CAS  Google Scholar 

  206. Weber, W. P., Gokel, G. W.: Phase transfer catalysis in Organic Chemistry, Berlin, Springer 1977

    Google Scholar 

  207. Hutchins, R. O., Natale, N. R., Cook, W. J.: Tetrahedron Lett. 1977 ,4167

    Google Scholar 

  208. Cacchi, S., La Torre, F., Misiti, D.: Synthesis 1979 ,356

    Google Scholar 

  209. Sundaraman, P., Herz, W.: J. Org. Chem. 42 ,813 (1977)

    Google Scholar 

  210. Overberger, C. G., Sannes, K. N.: Angew. Chem. Int. Ed. Engl. 13 ,99 (1974)

    Google Scholar 

  211. Cainelli, G., Cardillo, G., Orena, M., Sandri, S.: J. Am. Chem. Soc. 98 ,6737 (1976)

    CAS  Google Scholar 

  212. Frechet, J. M. J., Warnock, J., Farrall, M. J.: J. Org. Chem. 43 ,2618 (1978)

    CAS  Google Scholar 

  213. Fréchet, J. M. J., Derling, P., Farrall, M. J.: ibid. 46 ,1728 (1981)

    Google Scholar 

  214. Santaniello, E., Ponti, F., Manzocchi, A.: Synthesis 1978 ,534

    Google Scholar 

  215. Singh, R. P., Subbarao, H. N., Dev, S.: Tetrahedron 35 ,1789 (1979)

    CAS  Google Scholar 

  216. (a) Stairs, R. A., Diaper, D. G. M., Gatzke, A. L.: Can. J. Chem. 41 ,1059 (1963)

    CAS  Google Scholar 

  217. Cristol, S. J., Eilar, K. R.: J. Am. Chem. Soc., 72,4353 (1950)

    CAS  Google Scholar 

  218. San Filippo Jr., J., Chern, C. L: J. Org. Chem. 42 ,2182 (1977)

    Google Scholar 

  219. Cheng, Y. S., Liu, W. L., Chen, S.: Synthesis 1980 ,223

    Google Scholar 

  220. Platzer, N., De La Martiniere, B.: Bull. Soc. Chim. Fr. 1961, 111

    Google Scholar 

  221. Croft, R. C: Austr. J. Chem. 9, 201 (1956)

    CAS  Google Scholar 

  222. Lalancette, J. M., Rollin, G., Dumas, P.: J. Can. Chem. 50 ,3058 (1972)

    CAS  Google Scholar 

  223. Ebert, L. B., Huggins, R. A., Brauman, J. I.: Carbon 12 ,199 (1974)

    CAS  Google Scholar 

  224. Kagan, H. B.: CHEMTECH 1976 ,510

    Google Scholar 

  225. Westheimer, F. H., Novick, A.: J. Chem. Phys. 11 ,506 (1943)

    CAS  Google Scholar 

  226. For references see Wiberg, K. B.: Oxidation in Organic Chemistry, Part 4, N.Y., Academic Press, 1965

    Google Scholar 

  227. Holloway, F., Cohen, M., Westheimer, F.: J. Am. Chem. Soc. 73 ,65 (1951)

    CAS  Google Scholar 

  228. Led, A., Westheimer, F. H.: ibid. 74 ,4383 (1952)

    Google Scholar 

  229. Westheimer, F. H., Nicolaides, N.: ibid. 71 ,25 (1949)

    CAS  Google Scholar 

  230. Watanabe, W., Westheimer, F. H.: J. Chem. Phys. 17 ,61 (1949)

    CAS  Google Scholar 

  231. Rocek, J., Radkowsky, A. E.: J. Am. Chem. Soc. 90 ,2986 (1968)

    CAS  Google Scholar 

  232. Wiberg, K. E., Mukherjee, S. K.: ibid. 96 ,1884 (1974)

    CAS  Google Scholar 

  233. Cawley, J. J., Westheimer, F. H.: ibid. 85 ,1771 (1963)

    CAS  Google Scholar 

  234. Lee, D. G., Stewart, R.: J. Org. Chem. 32 ,2868 (1967)

    CAS  Google Scholar 

  235. Kwart, H., Nickle, J. H.: J. Am. Chem. Soc. 95 ,3394 (1973)

    CAS  Google Scholar 

  236. Cohen, M., Westheimer, F. H.: ibid. 95 ,4387 (1973)

    Google Scholar 

  237. Schreiber, J., Eschenmoser, A.: Helv. Chim. Acta 28 ,1529 (1955)

    Google Scholar 

  238. Kwart, H., Nickle, J. H.: J. Am. Chem. Soc. 96,1512 (1974)

    Google Scholar 

  239. Eliel, E., Schroeter, S. H., Brett, T. J., Biros, F. J., Richter, J. C: ibid. 88 ,3327 (1966)

    CAS  Google Scholar 

  240. Grimmer, G.: Liebigs Ann. Chem. 636 ,42 (1960)

    CAS  Google Scholar 

  241. Wilcox, C. F. Jr., Sexton, M., Wilcox, M. F.: J. Org. Chem. 28 ,1079 (1963)

    CAS  Google Scholar 

  242. Pasto, D. J., Rao, D. R.: J. Am. Chem. Soc. 92 ,5151 (1970)

    CAS  Google Scholar 

  243. Burstein, S. H., Ringold, H. J.: ibid. 89 ,4722 (1967)

    CAS  Google Scholar 

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  1. Istituto Chimico Giacomo Ciamician, Università degli Studi di Bologna, Via Selmi, 2, I-40126, Bologna, Italy

    Professor Gianfranco Cainelli & Professor Giuliana Cardillo

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  1. Professor Gianfranco Cainelli
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Cainelli, G., Cardillo, G. (1984). Oxidation of Alcohols. In: Chromium Oxidations in Organic Chemistry. Reactivity and Structure Concepts in Organic Chemistry, vol 19. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-69362-5_4

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