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Organic Syntheses pp 65–111Cite as

Formation and reactions of aminyloxides

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 59))

Abstract

The low energy content of the aminyloxide group is responsible for the easy formation of aminyloxides not only by a variety of simple reactions but also by many complex reactions. Besides various reactions of aminyloxides leading to the disappearance of radical function there are many reactions occurring at other functional groups in the molecule without the involvement of the aminyloxide function, hence retaining the radical character.

Only recently another type of reaction has been more extensively studied in which radical function is involved but finally retained. In these reactions the aminyloxide function disappears only temporarily during the course of reaction with subsequent regeneration. In contrast to reactions without involvement of the aminyloxide group these reactions should be named as reactions with participation and preservation of the aminyloxide function.

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References

  1. Piloty, O., Graf Schwerin, B.: Ber. Deut. Chem. Ges. 34, 1870 (1901)

    Google Scholar 

  2. Piloty, O., Graf Schwerin, B.: Ber. Deut. Chem. Ges. 34, 2354 (1901).

    Google Scholar 

  3. Wieland, H., Offenbächer, M.: Ber. Deut. Chem. Ges. 47, 2111 (1914).

    CAS  Google Scholar 

  4. Rozantsev, E. G.: Free nitroxyl radicals. New York-London: Plenum Press 1970.

    Google Scholar 

  5. Rozantsev, E. G., Sholle, V. D.: Synthesis 1971, 190

    Google Scholar 

  6. Rozantsev, E. G., Sholle, V. D.: Synthesis 1971, 401

    Google Scholar 

  7. Forrester, A. R., Hay, J. M., Thomson, R. H.: Organic chemistry of stable free radicals, p. 180. London and New York: Academic Press 1968; especially page 191.

    Google Scholar 

  8. Rozantsev, E. G.: Free nitroxyl radicals. New York-London: Plenum Press 1970 (especially pages 120–125).

    Google Scholar 

  9. Hayat, H., Silver, B. L.: J. Phys. Chem. 77, 72 (1973).

    Article  CAS  Google Scholar 

  10. Roberts, J. R., Ingold, K. U.: J. Am. Chem. Soc. 95, 3228 (1973).

    Article  CAS  Google Scholar 

  11. a) Cohen, A. H., Hoffman, B. M.: J. Phys. Chem. 78, 1313 (1974)

    Article  CAS  Google Scholar 

  12. Cohen, A. H., Hoffman, B. M.: J. Am. Chem. Soc. 95, 2061 (1973).

    CAS  Google Scholar 

  13. Faber, R. J.: J. Chem. Phys. 46, 1613 (1967).

    Article  Google Scholar 

  14. Baird, J. C.: J. Chem. Phys. 37, 1879 (1962).

    Article  CAS  Google Scholar 

  15. Aurich, H. G., Hahn, K., Stork, K., Weiss, W.: unpublished results.

    Google Scholar 

  16. Abronin, I. A., Sysoeva, N. A., Zhidomirov, G. M., Buchachenko, A. L., Chuvylkin, N. D.: Zh. Strukt. Khim. 12, 985 (1971); J. Struct. Chem. USSR (Engl. Transl.), 12, 907 (1971).

    CAS  Google Scholar 

  17. Andersen, B., Andersen, P.: Acta Chem. Scand. 20, 2728 (1966).

    CAS  Google Scholar 

  18. Berliner, L. J.: Acta Crystallogr. B 26, 1198 (1970).

    Google Scholar 

  19. Reichardt, Ch., Dimroth, K.: Fortschr. chem. forsch. 11, 1 (1968/1969); (especially page 50).

    CAS  Google Scholar 

  20. Aurich, H. G., Trösken, J.: Liebigs Ann. Chem. 745, 159 (1971).

    CAS  Google Scholar 

  21. Aurich, H. G., Dersch, W., Forster, H.: Chem. Ber. 106, 2854 (1973).

    CAS  Google Scholar 

  22. Janzen, E. G.: Acc. Chem. Res. 2, 279 (1969).

    Article  CAS  Google Scholar 

  23. Blackley, W. D.. Reinhard, R. R.: J. Am. Chem. Soc. 87, 802 (1965).

    Article  CAS  Google Scholar 

  24. loc. cit.4a) page 190 and cit.5) page 180 f.

    Google Scholar 

  25. Mahoney, L. R., Mendenhall, G. D., Ingold, K. U.: J. Am. Chem. Soc. 95, 8611 (1973).

    Article  Google Scholar 

  26. Stork, K.: Diss. Univ. Marburg 1974

    Google Scholar 

  27. Aurich, H. G., Stork, K.: Chem. Ber. 108, 2764 (1975).

    CAS  Google Scholar 

  28. Aurich, H. G., Baer, F.: Tetrahedron Letters 1965, 3879.

    Google Scholar 

  29. Hahn, K.: Dipl.-Arbeit, Univ. Marburg 1974

    Google Scholar 

  30. Aurich, H. G., Hahn, K., Stork, K.: Angew. Chem. 87, 590 (1975); Angew. Chem. Internat. Edit 14, 551 (1975).

    CAS  Google Scholar 

  31. Aurich, H. G., Dersch, W., Blinne, G.: Liebigs Ann. Chem. 762, 154 (1972).

    CAS  Google Scholar 

  32. Cowley, D. J., Waters, W. A.: J. Chem. Soc. (B), 1970, 96.

    Google Scholar 

  33. Cowley, D. J., Millen, M. H., Waters, W. A.: J. Chem. Soc. (B), 1971, 2393.

    Google Scholar 

  34. Millen, M. H., Waters, W. A.: J. Chem. Soc. (B), 1971, 2398.

    Google Scholar 

  35. West, R., Boudjouk, P.: J. Am. Chem. Soc. 93, 5901 (1971).

    CAS  Google Scholar 

  36. loc. cit.4a) and cit.5): page 185.

    Google Scholar 

  37. Toda, T., Mori, E., Horiuchu, H., Murayama, K.: Bull. Chem. Soc. Jap. 45, 1802 (1972).

    CAS  Google Scholar 

  38. Neugebauer, F. A., Fischer, P. H. H.; Chem. Ber. 98, 844 (1965)

    CAS  Google Scholar 

  39. Fischer, P. H. H., Neugebauer, F. A.: Z. Naturforsch. 19A, 1514 (1964).

    CAS  Google Scholar 

  40. Nelsen, S. F., Landis, II, R. T.: J. Am. Chem. Soc. 95, 8707 (1973).

    CAS  Google Scholar 

  41. Danen, W. C., West, C. T., Kensler, T. T.: J. Am. Chem. Soc. 95, 5716 (1973).

    CAS  Google Scholar 

  42. loc. cit.3), page 67.

    Google Scholar 

  43. Boozev, Ch. E., Hammond, G. S.: J. Am. Chem. Soc. 76, 3861 (1954)

    Google Scholar 

  44. Thomas, J. R., Tolman, C. A.: J. Am. Chem. Soc. 84, 2930 (1962).

    CAS  Google Scholar 

  45. Janzen, E. G.: Acc. Chem. Res. 4, 31 (1971).

    Article  CAS  Google Scholar 

  46. Forrester, A. R., Hepburn, S. P.: J. Chem. Soc. (C), 1971, 701.

    Google Scholar 

  47. Holman, R. J., Perkins, M. J.: J. Chem. Soc. (C), 1971, 2324.

    Google Scholar 

  48. Lagercrantz, C., Torsell, K.: Acta Chem. Scand. 22, 1935 (1965).

    Google Scholar 

  49. Hartgerink, J. W., Engberts, J. B. F. N., Wajer, Th. A. J., de Boer, Th. J.: Rec. Trav. Chim. Pays-Bas 88, 481 (1969).

    CAS  Google Scholar 

  50. Stammer, R., Engberts, J. B. F. N., de Boer, Th. J.: Rec. Trav. Chim. Pays-Bas 89, 169 (1970).

    CAS  Google Scholar 

  51. Terabe, S., Kuruma, K., Konaka, R.: JCS Perkin II, 1973, 1252.

    Google Scholar 

  52. Terabe, S., Konaka, R.: JCS Perkin II, 1973, 369

    Google Scholar 

  53. Terabe, S., Konaka, R.: Bull. Chem. Soc. Jap. 46, 825 (1973).

    CAS  Google Scholar 

  54. Ahrens, W., Wieser, K., Berndt, A.: unpublished results

    Google Scholar 

  55. Ahrens, W., Wieser, K., Berndt, A.: Tetrahedron Letters 1973, 3141.

    Google Scholar 

  56. Cheng, I.-D., Shine, H. J.: J. Org. Chem. 39, 336 (1974)

    CAS  Google Scholar 

  57. Edwards, O. E., Paskovich, D. H., Reddoch, A. H.: Can. J. Chem. 51, 978 (1973)

    CAS  Google Scholar 

  58. Terabe, S., Konaka, R.: JCS Perkin II, 1972, 2163

    Google Scholar 

  59. Terabe, S., Konaka, R.: J. Am. Chem. Soc. 91, 5655 (1969)

    Article  CAS  Google Scholar 

  60. Lagererantz, C., Forshult, S.: Acta Chem. Scand. 23, 708 (1969)

    Google Scholar 

  61. Leaver, J. H., Ramsay, G. C., Suzuki, E.: Austr. J. Chem. 22, 1891 (1969)

    CAS  Google Scholar 

  62. Leaver, J. H., Ramsay, G. C.: Austr. J. Chem. 22, 1899 (1969).

    CAS  Google Scholar 

  63. Mackor, A., Wajer, Th. A. J. W., de Boer, Th. J.: Tetrahedron Letters 1967, 385

    Google Scholar 

  64. Wargon, J. A., Williams, F.: J. Am. Chem. Soc. 94, 7917 (1972)

    Article  CAS  Google Scholar 

  65. Forshult, S., Lagererantz, C.: Acta Chem. Scand. 23, 522 (1969)

    CAS  Google Scholar 

  66. Perkins, M. J., Ward, P., Horsfield, A.: J. Chem. Soc. (B), 1970, 395

    Google Scholar 

  67. Abakumov, G. A., Razuvaev, G. A.: Dokl. Akad. Nauk SSSR 182, 95 (1968); C. A. 70, 2968 (1969).

    CAS  Google Scholar 

  68. Karlsson, H., Lagererantz, C.: Acta Chem. Scand. 24, 3411 (1970)

    CAS  Google Scholar 

  69. Adevik, G., Lagererantz, C.: Acta Chem. Scand. 24, 2253 (1970)

    CAS  Google Scholar 

  70. Boekestein, G., Buck, H. M.: Rec. Trav. Chim. Pays-Bas 92, 1095 (1973).

    CAS  Google Scholar 

  71. Mulvey, D., Waters, W. A.: JCS Perkin II, 1974, 666.

    Google Scholar 

  72. Mackor, A., Wajer, Th. A. J. W., de Boer, Th. J., van Voorst, J. D. W.: Tetrahedron Letters 1966, 2115.

    Google Scholar 

  73. Wajer, Th. A. J. W., Mackor, A., de Boer, Th. J., van Voorst, J. D. W.: Tetrahedron 23, 4021 (1967).

    Article  CAS  Google Scholar 

  74. Carmichael, P. J., Gowenlock, B. G., Johnson, C. A. F.: JCS Perkin II, 1973, 1853.

    Google Scholar 

  75. Maassen, J. A., Hittenhausen, H., de Boer, Th. J.: Tetrahedron Letters 1971, 3213.

    Google Scholar 

  76. Rassat, A., Rey, P.: Chem. Commun. 1971, 1161.

    Google Scholar 

  77. Malatesta, V., Ingold, K. U.: Tetrahedron Letters 1973, 3307

    Google Scholar 

  78. Maassen, J. A., de Boer, Th. J.: Rec. Trav. Chim. Pays-Bas 92, 185 (1973)

    CAS  Google Scholar 

  79. Aurich, H. G., Dersch, W.: Z. Naturforsch. 28B, 525 (1973).

    Google Scholar 

  80. Chalfont, G. R., Perkins, M. J., Horsfield, A.: J. Am. Chem. Soc. 90, 7141 (1968).

    Article  CAS  Google Scholar 

  81. Jonkman, L., Muller, H., Kommandeur, J.: J. Am. Chem. Soc. 93, 5833 (1971).

    Article  CAS  Google Scholar 

  82. Motherwell, W. B., Roberts, J. S.: JCS Chem. Commun. 1972, 328.

    Google Scholar 

  83. Camaggi, C. M., Holman, R. J., Perkins, M. J.: JCS Perkin II, 1972, 501.

    Google Scholar 

  84. Cadogan, J. I. G.: Acc. Chem. Res. 4, 186 (1971).

    Article  CAS  Google Scholar 

  85. Chalfont, G. R., Perkins, M. J.: J. Am. Chem. Soc. 89, 3054 (1967).

    Article  CAS  Google Scholar 

  86. Wajer, Th. A. J. W., Mackor, A., de Boer, Th. J.: Tetrahedron 25, 175 (1969).

    Article  CAS  Google Scholar 

  87. Russell, G. A., Geels, E. J., Smentowski, F. J., Chang, K.-Y., Reynolds, J., Kaupp, G.: J. Am. Chem. Soc. 89, 3821 (1967).

    CAS  Google Scholar 

  88. Mulvey, D., Waters, W. A.: JCS Perkin II, 1974, 772.

    Google Scholar 

  89. loc. cit.5), page 181.

    Google Scholar 

  90. Ashby, E. C., Laemmle, J., Neumann, H. M.: Acc. Chem. Res. 7, 272 (1974).

    Article  CAS  Google Scholar 

  91. Regenstein, H.: Diss. Univ. Marburg 1974

    Google Scholar 

  92. Berndt, A., Regenstein, H.: unpublished results.

    Google Scholar 

  93. Aurich, H. G., Baer, F.: Angew. Chem. 79, 1070 (1967); Angew. Chem. Internat. Edit. 6, 1080 (1967).

    Google Scholar 

  94. Sullivan, A. B.: J. Org. Chem. 31, 2811 (1966)

    CAS  Google Scholar 

  95. Knight, G. T.: Chem. Commun. 1970, 1016.

    Google Scholar 

  96. Banks, R. E., Haszeldine, R. N., Miller, P. J.: Tetrahedron Letters 1970, 4417.

    Google Scholar 

  97. Layer, R. W.: Tetrahedron Letters 1970, 4413.

    Google Scholar 

  98. a) Wassmuth, G.: Diss. Univ. Marburg 1974

    Google Scholar 

  99. Aurich, H. G., Wassmuth, G.: unpublished results.

    Google Scholar 

  100. Lewis, J. W., Myers, P. L., Ormerod, J. A.: JCS Perkin I, 1972, 2521

    Google Scholar 

  101. Lewis, J. W., Myers, P. L. Ormerod, J. A.: JCS Perkin I, 1973, 1129.

    Google Scholar 

  102. Wajer, Th. A. J. W., Geluk, H. W., Engberts, J. B. F. N., de Boer, Th. J.: Rec. Trav. Chim. Pays-Bas 89, 696 (1970).

    CAS  Google Scholar 

  103. Lakatos, B., Turcsanyi, B., Tüdos, F.: Acta Chim. Acad. Sci. Hung, 70, 225 (1971): C. A. 76, 125960 (1972).

    CAS  Google Scholar 

  104. Banks, R. E., Edge, D. J., Freear, J., Haszeldine, R. N.: JCS Perkin I, 1974, 721.

    Google Scholar 

  105. Janzen, E. G., Gerlock, J. L.: J. Am. Chem. Soc. 91, 3108 (1969)

    CAS  Google Scholar 

  106. Cowley, D. J., Sutcliffe, L. H.: J. Chem. Soc (B), 1970, 569.

    Google Scholar 

  107. McMillan, M., Norman, R. O. C.: J. Chem. Soc (B), 1968, 590

    Google Scholar 

  108. Anderson, N. H., McMillan, M., Norman, R. O. C.: ibid. 1970, 1075.

    Google Scholar 

  109. Chachaty, C., Forchioni, A.: Tetrahedron Letters 1968, 307.

    Google Scholar 

  110. Chachaty, C., Forchioni, A.: Tetrahedron Letters 1968, 1079.

    Google Scholar 

  111. Ahrens, W., Berndt, A.: Tetrahedron Letters 1973, 4281

    Google Scholar 

  112. Ahrens, W., Berndt, A.: unpublished results

    Google Scholar 

  113. Camaggi, C. M., Lunazzi, L., Placucci, G.: J. Org. Chem. 39, 2425 (1974)

    Article  CAS  Google Scholar 

  114. Camaggi, C. M., Leardini, R., Placucci, G.: JCS Perkin II, 1974, 1195

    Google Scholar 

  115. Camaggi, C. M., Lunazzi, L., Pedulli, G. F., Placucci, G., Tiecco, M.: JCS Perkin II, 1974, 1226.

    Google Scholar 

  116. Chalfont, G. R., Hey, D. H., Liang, K. S. Y., Perkins, M. J.: J. Chem. Soc. (B), 1971, 233.

    Google Scholar 

  117. Beckwith, A. L. J., Lawton, M. D.: JCS Perkin II, 1973, 2134.

    Google Scholar 

  118. Hoffmann, A. K., Feldmann, A. M., Gelblum, E., Hodgson, W. G.: J. Am. Chem. Soc. 86, 639 (1964)

    CAS  Google Scholar 

  119. Hoffmann, A. K., Hodgson, W. G., Maricle, D. L., Jura, W. H.: J. Am. Chem. Soc. 86, 631 (1964).

    CAS  Google Scholar 

  120. Hoffmann, A. K., Feldmann, A. M., Gelblum, E.: J. Am. Chem. Soc. 86, 646 (1964).

    CAS  Google Scholar 

  121. loc. cit.5); page 182.

    Google Scholar 

  122. Perkins, M. J. in: Essays on free-radical chemistry (ed. R. O. C. Norman): Chem. Soc. Special Publ. 24, 97 (1970).

    Google Scholar 

  123. Janzen, E. G., Blackburn, B. J.: J. Am. Chem. Soc. 91, 4481 (1969).

    CAS  Google Scholar 

  124. Bluhm, A. L., Weinstein, J.: J. Org. Chem. 37, 1748 (1972)

    Article  CAS  Google Scholar 

  125. Janzen, E. G., Evans, C. A.: J. Am. Chem. Soc. 95, 8205 (1973)

    Article  CAS  Google Scholar 

  126. Janzen, E. G., Evans, C. A., Nishi, Y.: J. Am. Chem. Soc. 94, 8236 (1972).

    Article  CAS  Google Scholar 

  127. Chalfont, G. R., Perkin, M. J., Horsfield, A.: J. Chem. Soc. (B), 1970, 401

    Google Scholar 

  128. Aurich, H. G., Höhlein, P.: Tetrahedron Letters 1974, 279.

    Google Scholar 

  129. Iwamura, M., Inamoto, N.: Bull. Chem. Soc. Jap. 40, 703 (1967)

    CAS  Google Scholar 

  130. Iwamura, M., Inamoto, N.: Bull. Chem. Soc. Jap. 43, 860 (1970)

    CAS  Google Scholar 

  131. Janzen, E. G., Liu, J. I.-P.: J. Magn. Res. 9, 510 (1973)

    CAS  Google Scholar 

  132. Janzen, E. G., Evans, C. A., Liu, J. I.-P.: J. Magn. Res. 9, 513 (1973).

    CAS  Google Scholar 

  133. Tyurikov, V. A., Shapiro, B. I., Neimann, L. A.: Zh. Org. Khim. 7, 2372 (1971); J. Org. Chem. USSR (Engl. Transl.) 7, 2463 (1971).

    CAS  Google Scholar 

  134. Janzen, E. G., Lopp, J. G.: J. Magn. Res. 7, 107 (1972).

    CAS  Google Scholar 

  135. Bard, A. J., Gilbert, J. C., Goodin, R. D.: J. Am. Chem. Soc. 96, 620 (1974).

    Article  CAS  Google Scholar 

  136. Pacifici, J. G., Browning, Jr., H. L.: J. Am. Chem. Soc. 92, 5231 (1970).

    Article  CAS  Google Scholar 

  137. Camaggi, C. M., Perkins, M. J.: JCS Perkin II, 1972, 507.

    Google Scholar 

  138. Höhlein, P.: Diss. Univ. Marburg 1974

    Google Scholar 

  139. Aurich, H. G., Höhlein, P.: unpublished results.

    Google Scholar 

  140. Bluhm, A. L., Weinstein, J.: J. Am. Chem. Soc. 92, 1444 (1970).

    Article  CAS  Google Scholar 

  141. Sommermeyer, K., Seiffert, W., Wilker, W.: Tetrahedron Letters 1974, 1821.

    Google Scholar 

  142. Eckersley, A., Rogers, N. A. J.: Tetrahedron Letters 1974, 1661.

    Google Scholar 

  143. Caragheorgheopol, A., Căldăraru, H., Constantinescu, T., Em Sahini, V.: J. Am. Chem. Soc. 93, 6766 (1971)

    Article  CAS  Google Scholar 

  144. Lown, J. B.: J. Chem. Soc. (B), 1966, 441

    Google Scholar 

  145. Lown, J. B.: J. Chem. Soc. (B), 1966, 644.

    Google Scholar 

  146. Wajer, Th. A. J. W., Mackor, A., de Boer, Th. J., van Voorst, J. D. W.: Tetrahedron 23, 4021 (1967).

    Article  CAS  Google Scholar 

  147. Smith, P., Fox, W. M.: Can. J. Chem. 47, 2227 (1969)

    CAS  Google Scholar 

  148. Adams, J. Q.: J. Am. Chem. Soc. 89, 6022 (1967).

    Article  CAS  Google Scholar 

  149. Khadzhiev, D. S., Todorova-Khadzhieva, E. S.: Dokl. Bolg. Akad. Nauk 25, 507 (1972); C. A. 77, 114 226 (1972).

    CAS  Google Scholar 

  150. review article: Griffith, O. H., Waggoner, A. S.: Acc. Chem. Res. 2, 17 (1969).

    Article  CAS  Google Scholar 

  151. Gramicidin, S., Ivanov, V. T., Miroshnikov, A. I., Snezhkova, L. G., Ovchinnikov, Yu. A., Kulikov, A. V., Likhtenshtein, G. I.: Khim. Prir. Soedin. 9, 91 (1973); C. A. 79, 19077 (1973).

    Google Scholar 

  152. Osiecki, J. H., Ullman, E. F.: J. Am. Chem. Soc. 90, 1078 (1968).

    Article  CAS  Google Scholar 

  153. Boocock, D. G. B., Darcy, R., Ullman, E. F.: J. Am. Chem. Soc. 90, 5945 (1968)

    CAS  Google Scholar 

  154. Boocock, D. G. B., Ullman, E. F.: J. Am. Chem. Soc. 90, 6873 (1968).

    CAS  Google Scholar 

  155. Ullman, E. F., Boocock, D. G. B.: Chem. Commun. 1969, 1161.

    Google Scholar 

  156. Ullman, E. F., Call, L., Leute, R. K., Osiecki, J. H.: U. S. 3, 740, 412; C. A. 79, 42502 (1973).

    Google Scholar 

  157. Darcy, R., Ullman, E. F.: J. Am. Chem. Soc. 91, 1024 (1969).

    Article  CAS  Google Scholar 

  158. Ullman, E. F., Osiecki, J. H., Boocock, D. G. B., Darcy, R.: J. Am. Chem. Soc. 94, 7049 (1972).

    CAS  Google Scholar 

  159. Ullman, E. F., Call, L., Osiecki, J. H.: J. Org. Chem. 35, 3623 (1970).

    Article  CAS  Google Scholar 

  160. Wagner, B. E., Helbert, J. N., Bates, Jr., R. D., Poindexter, E. H.: JCS Chem. Commun. 1973, 748.

    Google Scholar 

  161. Medzhidov, A. A., Kirichenko, L. N., Likhtenshtein, G. I.: Izv. Akad. Nauk SSSR, Ser. Khim. 1969, 698; C. A. 71, 49713 (1969).

    Google Scholar 

  162. Hartgerink, J. W., Engberts, J. B. F. N., de Boer, Th. J.: Tetrahedron Letters 1971, 2709

    Google Scholar 

  163. Holman, R. J., Perkins, M. J.: Chem. Commun. 1971, 244

    Google Scholar 

  164. Aurich, H. G., Stork, K.: Tetrahedron Letters 1972, 555.

    Google Scholar 

  165. Weiss, W.: Diss. Univ. Marburg 1973

    Google Scholar 

  166. Aurich, H. G., Weiss, W.: Tetrahedron in press.

    Google Scholar 

  167. Arndt, F., Eistert, B., Pertale, W.: Ber. Deut. Chem. Ges. 60, 1364 (1927).

    Google Scholar 

  168. loc. cit.5); especially page 221 ff.

    Google Scholar 

  169. Sholle, V. D., Golubev, V. A., Rozantsev, E. G.: Dokl. Akad. Nauk SSSR 200, 137 (1971); Dokl. Chem. (Engl. Transl.) 200, 761 (1971).

    CAS  Google Scholar 

  170. Robbins, W. K., Eastman, R. H.: J. Am. Chem. Soc. 92, 6077 (1970).

    CAS  Google Scholar 

  171. Rykov, S. V., Sholle, V. D.: Izv. Akad. Nauk SSSR, Ser. Khim. 1971, 2351; C. A. 76, 45448 (1972).

    Google Scholar 

  172. loc. cit.4b); (especially page 406).

    Google Scholar 

  173. Keana, J. F. W., Dinerstein, R. J., Baitis, F.: J. Org. Chem. 36, 209 (1971).

    CAS  Google Scholar 

  174. Murayama, K., Yoshioka, T.: Bull. Chem. Soc. Jap. 42, 2307 (1969)

    CAS  Google Scholar 

  175. Yoshioka, T., Higashida, S., Morimura, S., Murayama, K.: Bull. Chem. Soc. Jap. 44, 2207 (1971).

    CAS  Google Scholar 

  176. Schlude, H.: Tetrahedron 29, 4007 (1973)

    Article  CAS  Google Scholar 

  177. Kabs, K.: Diss. Univ. Marburg 1970.

    Google Scholar 

  178. Toda, T., Mori, E., Murayama, K.: Bull. Chem. Soc. Jap. 45, 1904 (1972).

    CAS  Google Scholar 

  179. Banks, R. E., Haszeldine, R. N., Stevenson, M. J.: J. Chem. Soc. (C), 1966, 901.

    Google Scholar 

  180. Banks, R. E., Justin, B., Haszeldine, R. N.: J. Chem. Soc. (C), 1971, 2777

    Google Scholar 

  181. Banks, R. E., Chondhury, D. R., Haszeldine, R. N.: JCS Perkin I, 1973, 1092.

    Google Scholar 

  182. Banks, R. E., Chondhury, D. R., Haszeldine, R. N.: JCS Perkin I, 1973, 80.

    Google Scholar 

  183. Banks, R. E., Haszeldine, R. N., Myerscough, T.: JCS Perkin I, 1972, 2336.

    Google Scholar 

  184. Banks, R. E., Haszeldine, R. N., Myerscough, T.: J. Chem. Soc. (C) 1971, 1951.

    Google Scholar 

  185. Banks, R. E., Haszeldine, R. N., Stephens, C. W.: Tetrahedron Letters 1972, 3699.

    Google Scholar 

  186. Banks, R. E., Cheng, W. M., Haszeldine, R. N., Show, G.: J. Chem. Soc. (C), 1970, 55.

    Google Scholar 

  187. Mendenhall, G. D., Ingold, K. U.: J. Am. Chem. Soc. 95, 6390 (1973).

    CAS  Google Scholar 

  188. Capiomont, A., Chion, B., Lajzerowicz, J.: Acta Cristallogr. B27, 322 (1971).

    Google Scholar 

  189. Ramasseul, R., Rassat, A., Rio, G., Scholl, M.-J.: Bull. Soc. Chim. Fr. 1971, 215.

    Google Scholar 

  190. Moser, W., Howie, R. A.: J. Chem. Soc. (A), 1968, 3039.

    Google Scholar 

  191. Mendenhall, G. D., Ingold, K. U.: J. Am. Chem. Soc. 95, 6395 (1973).

    CAS  Google Scholar 

  192. Dupeyre, R. M., Rassat, A.: J. Am. Chem. Soc. 88, 3180 (1966)

    Article  CAS  Google Scholar 

  193. loc. cit4b), page 401.

    Google Scholar 

  194. Adamic, K., Bowman, D. F., Ingold, K. U.: J. Am. Chem. Soc. 92, 1093 (1970)

    CAS  Google Scholar 

  195. Adamic, K., Bowman, D. F., Gillan, T., Ingold, K. U.: J. Am. Chem. Soc. 93, 902 (1971).

    Google Scholar 

  196. Bowman, D. F., Brokenshire, J. L., Gillan, T., Ingold, K. U.: J. Am. Chem. Soc. 93, 6551

    Google Scholar 

  197. Bowman, D. F., Gillan, T., Ingold, K. U.: J. Am. Chem. Soc. 93, 6555 (1971).

    CAS  Google Scholar 

  198. Martinie-Hombrouck, J., Rassat, A.: Tetrahedron 30, 433 (1974).

    Article  CAS  Google Scholar 

  199. Woodward, R. B., Wintner, C.: Tetrahedron Letters 1969, 2693

    Google Scholar 

  200. Lotz, I.: Dipl.-Arbeit, Univ. Marburg 1974

    Google Scholar 

  201. Aurich, H. G., Lotz, I., Weiss, W.: unpublished results.

    Google Scholar 

  202. Wicland, H., Roth, K.: Ber. Deut. Chem. Ges. 53, 210 (1920).

    Google Scholar 

  203. Calder, A., Forrester, A. R.: Chem. Commun. 1967, 682.

    Google Scholar 

  204. Forrester, A. R., Hepburn, S. P.: J. Chem. Soc. (C), 1970, 1277.

    Google Scholar 

  205. Forrester, A. R., Hepburn, S. P.: J. Chem. Soc. (C), 1971, 3322.

    Google Scholar 

  206. Calder, A., Forrester, A. R., Hepburn, S. P.: JCS Perkin I, 1973, 456.

    Google Scholar 

  207. Abramovitch, R. A., Challand, S. R.: J. Heterocycl. Chem. 10, 683 (1973).

    CAS  Google Scholar 

  208. Eames, T. B., Hoffman, B. M.: J. Am. Chem. Soc. 93, 3141 (1971)

    Google Scholar 

  209. Cazianis, C. T., Eaton, D. R.: Can. J. Chem. 52, 2463 (1974).

    CAS  Google Scholar 

  210. Hoffman, B. M., Eames, T. B.: J. Am. Chem. Soc. 91, 5168 (1969)

    CAS  Google Scholar 

  211. Abakumov, G. A., Tikhonov, V. D., Razuyald, G. A.: Dokl. Akad. Nauk SSSR 187, 571 (1969); C. A. 71, 85129 (1969)

    CAS  Google Scholar 

  212. Razuvaev, G. A., Tikhonov, V. D., Abakumov, G. A.: Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 1732; C. A. 74, 59210 (1971).

    Google Scholar 

  213. Abakumov, G. A., Tikhonov, V. D.: Zh. Strukt. Khim. 13, 150 (1972); J. Strukt. Chem. USSR (Engl. Transl.) 13, 136 (1972).

    Google Scholar 

  214. Cazianis, C. T., Eaton, D. R.: Can. J. Chem. 52, 2454 (1974)

    CAS  Google Scholar 

  215. Wilbur, D., Kreilick, R.: J. Chem. Phys. 52, 1643 (1970)

    Article  CAS  Google Scholar 

  216. Zelonka, R. A., Baird, M. C.: Chem. Commun. 1970, 1448

    Google Scholar 

  217. Brown, D. G., Maier, T., Drago, R. S.: Inorg. Chem. 10, 2804 (1971).

    CAS  Google Scholar 

  218. Hoffman, B. M., Eames, T. B.: J. Am. Chem. Soc. 91, 2169 (1969)

    CAS  Google Scholar 

  219. Brackman, W., Gaasbeck, C. J.: Rec. Trav. Chim. Pays-Bas 85, 221 (1966)

    CAS  Google Scholar 

  220. Abakumov, G. A., Tikhonov, V. D.: Izv. Akad. Nauk SSSR, Ser. Khim. 1969, 796; C. A. 71, 22004 (1969).

    Google Scholar 

  221. Malatesta, U., Ingold, K. U.: J. Am. Chem. Soc. 95, 6404 (1973).

    CAS  Google Scholar 

  222. Murata, Y., Mataga, N.: Bull. Chem. Soc. Jap. 44, 354 (1971).

    Google Scholar 

  223. McConnell, A. A., MacNicol, D. D., Porte, A. L.: J. Chem. Soc. (A), 1971, 3516.

    Google Scholar 

  224. Kabankin, A. S., Zhidomirov, G. M., Buchachenko, A. L.: J. Magn. Resonance 9, 199 (1973).

    CAS  Google Scholar 

  225. Lozos, G. P., Hoffman, B. M.: J. Phys. Chem. 78, 200 (1974).

    CAS  Google Scholar 

  226. Hogeveen, H., Gersmann, H. R., Praat, A. P.; Rec. Trav. Chim. Pays-Bas 86, 1063 (1967)

    CAS  Google Scholar 

  227. Golubev, V. A., Zhdanov, R. I., Gida, V. M., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1971, 853; C. A. 75, 63751 (1971).

    Google Scholar 

  228. Golubev, V. A., Zhdanov, R. I., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 184; C. A. 72, 111229 (1970)

    Google Scholar 

  229. Zhdanov, R. I., Golubev, V. A., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 176; C. A. 72, 111227 (1970).

    Google Scholar 

  230. Golubev, V. A., Voronina, G. N., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 2605; C. A. 74, 111841 (1971)

    Google Scholar 

  231. Golubev, V. A., Voronina, G. N., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 161; C. A. 77, 34321 (1972).

    Google Scholar 

  232. Golubev, V. A., Voronina, G. N.: Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 164; C. A. 77, 34322 (1972)

    Google Scholar 

  233. Golubev, V. A., Sholle, V. D., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 1202; C. A. 77, 114165 (1972)

    Google Scholar 

  234. Sholle, V. D., Golubev, V. A., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 1204; C. A. 77, 114169 (1972).

    Google Scholar 

  235. Golubev, V. A., Zhdanov, R. I., Gida, V. M., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 2815; C. A. 74, 111325 (1971).

    Google Scholar 

  236. Golubev, V. A., Zhdanov, R. I., Protsishin, I. T., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 2158; C. A. 74, 76280 (1971).

    Google Scholar 

  237. Cadogan, J. I. G., Rowley, A. G.: JCS Chem. Commun. 1974, 179.

    Google Scholar 

  238. Levenson, J. L., Kaplan, L.: JCS Chem. Commun. 1974, 23.

    Google Scholar 

  239. Kornblum, N., Pinnick, H. W.: J. Org. Chem. 37, 2050 (1972).

    Article  CAS  Google Scholar 

  240. Zhdanov, R. I., Golubev, V. A., Gida, V. M., Rozantsev, E. G.: Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 2396; C. A. 74, 141461 (1971).

    Google Scholar 

  241. Golubev, V. A.: Izv. Akad. Nauk SSSR, Ser. Khim. 1971, 890; C. A. 75, 48843 (1971).

    Google Scholar 

  242. Janzen, E. G. in: Topics in stereochemistry (eds. N. L. Allinger and E. L. Eliel), Vol. 6, page 177. New York: Wiley-Interscience 1971.

    Google Scholar 

  243. Iwamura, N., Inamoto, N.: Bull. Chem. Soc. Jap. 43, 860 (1970).

    CAS  Google Scholar 

  244. Minisci, F., Galli, R., Quilico, A.: Tetrahedron Letters 1963, 785.

    Google Scholar 

  245. Gowenlock, B. G., Pfab, J., Kresze, G.: JCS Perkin II, 1974, 511.

    Google Scholar 

  246. Aurich, H. G., Weiss, W.: Chem. Ber. 105, 2389 (1972).

    CAS  Google Scholar 

  247. Weiss, W.: Diss. Univ. Marburg 1973

    Google Scholar 

  248. Aurich, H. G., Weiss, W.: Liebigs Ann. Chem., submitted for publication.

    Google Scholar 

  249. Call, L., Ullman, E. F.: Tetrahedron Letters 1973, 961.

    Google Scholar 

  250. Aurich, H. G., Kabs, K.: Angew. Chem. 82, 634 (1970); Angew. Chem. internat. Ed. 9, 636 (1970).

    Google Scholar 

  251. Maender, O. W., Janzen, E. G.: J. Org. Chem. 34, 4072 (1969).

    Article  CAS  Google Scholar 

  252. Craig, R. L., Roberts, J. S.: JCS Chem. Commun. 1972, 1142.

    Google Scholar 

  253. Craig, R. L., Murray-Rust, J., Murray-Rust, P., Roberts, J. S.: JCS Chem. Commun. 1973, 751.

    Google Scholar 

  254. Forrester. A. R., Ogilvy, M. M., Thomson, R. H.: J. Chem. Soc. (C), 1970, 1081

    Google Scholar 

  255. loc. cit.5), page 215.

    Google Scholar 

  256. Perkins, M. J., Ward, P.: JCS Chem. Commun. 1973, 883.

    Google Scholar 

  257. Keana, J. F. W., Baitis, F.: Tetrahedron Letters 1968, 365.

    Google Scholar 

  258. Ullman, E. F., Call, L., Tseng, S. S.: J. Am. Chem. Soc. 95, 1677 (1973).

    Article  CAS  Google Scholar 

  259. Nelsen, S. F., Landis, II, R. T.: J. Am. Chem. Soc. 95, 6454 (1973).

    Google Scholar 

  260. Balaban, A. T., Negoită, N., Baican, R.: J. Magn. Res. 9, 1 (1973).

    CAS  Google Scholar 

  261. Razuvaev, G. A., Abakumov, G. A., Cherkasov, V. K.: Dokl. Akad. Nauk SSSR 198, 601 (1971); Dokl. Chem. (Engl. Transl.) 198, 439 (1971)

    CAS  Google Scholar 

  262. Abakumov, G. A., Cherkasov, V. K., Razuvaev, G. A.: Dokl. Akad. Nauk SSSR 197, 823 (1971); Dokl. Chem. (Engl. Transl.) 197, 265 (1971).

    CAS  Google Scholar 

  263. Grigo, U.: Diss. Univ. Marburg 1974

    Google Scholar 

  264. Aurich, H. G., Grigo, U.: unpublished results.

    Google Scholar 

  265. Aurich, H. G., Weiss, W.: Chem. Ber. 106, 2408 (1973).

    CAS  Google Scholar 

  266. Küttner, G.; Dipl.-Arbeit, Univ. Marburg 1974

    Google Scholar 

  267. Aurich, H. G., Küttner, G.: unpublished results.

    Google Scholar 

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  1. Fachbereich Chemie der Philipps-Universität Marburg, Deutschland

    Prof. Dr. Hans Günter Aurich & Dr. Wolfram Weiss

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  1. Prof. Dr. Hans Günter Aurich
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R. D. Rieke J. A. Zoltewicz H. G. Aurich W. Weiss K. P. C. Vollhardt

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Dedicated to Prof. Dr. K. Dimroth on the occasion of his 65th birthday

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Aurich, H.G., Weiss, W. (1975). Formation and reactions of aminyloxides. In: Rieke, R.D., Zoltewicz, J.A., Aurich, H.G., Weiss, W., Vollhardt, K.P.C. (eds) Organic Syntheses. Topics in Current Chemistry, vol 59. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0046187

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