Preparation of tetramethylpiperdine-1-oxoammonlum salts and their use as oxidants in organic chemistry. A review

Organic Preparations and Procedures International

Volumn 36, Issue 1, 2004, Pages 1-31

  Merbouh, Nabyl ^a   Bobbitt, James M ^a   Brückner, Christian ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC CHEMISTRY;

ACETAL DERIVATIVE; ACID ANHYDRIDE; ALCOHOL; BENZOIC ACID DERIVATIVE; BETA LACTAM DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ETHER DERIVATIVE; FREE RADICAL; GLUCOSE; GLUTARIC ACID; HYDROXYLAMINE; INDOLE DERIVATIVE; INORGANIC SALT; NITROXIDE DERIVATIVE; OXIDIZING AGENT; PIPERIDINE DERIVATIVE; POLYSACCHARIDE; SULFIDE; SULFOXIDE; THREONINE;

ALCOHOL OXIDATION; BAEYER VILLIGER REACTION; BENZYLATION; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DIHYDROXYLATION; ESTERIFICATION; ETHERIFICATION; GLUCOSE OXIDATION; ORGANIC CHEMISTRY; PRECURSOR; QUANTUM YIELD; REACTION ANALYSIS; REVIEW; SACCHARIFICATION; STOICHIOMETRY; STRUCTURE ANALYSIS; SULFATION; SYNTHESIS;

EID: 1642373717     PISSN: 00304948     EISSN: 19455453     Source Type: Journal    
DOI: 10.1080/00304940409355369     Document Type: Review

References (130)

1. V. A. Golubev, E. G. Rozantsev, and M. B. Neiman, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1898 (Engl. Transl.) (1965);
2. V. A. Golubev, E. G. Rozantsev, and M. B. Neiman, Chem. Abstr., 64, 59770 (1966).
3. E. G. Rozantsev and V. D. Sholle, Synthesis, 190 (1971).
4. E. G. Rozantsev and V. D. Sholle, Synthesis, 401 (1971).
5. J. F. W. Keana, Chem. Rev., 78, 37 (1978).
6. J. M. Bobbitt and M. C. L. Flores, Heterocycles, 27, 509 (1988).
7. A. E. J. de Nooy, A. C. Besemer, and H. van Bekkum, Synthesis, 1153 (1996).
8. F. Francis, J. Chem. Soc., 2897 (1927).
9. G. Sosnovsky and M. Konieczny, Synthesis, 735 (1976).
10. G. Sosnovsky and M. Konieczny, Z Naturforsch., 32b, 328 (1977).
11. G. Sosnovsky and M. Konieczny, Z. Naturforsch., 32b, 338 (1977).
12. Z. Ma, Q. Huang, and J. M. Bobbitt, J. Org. Chem., 58, 4837 (1993).
13. K. Murayama, S. Morimura, O. Amakasu, T. Toda, and E. Yamao, Nippon Kagaku Zasshi, 90, 296 (1969);
14. K. Murayama, S. Morimura, O. Amakasu, T. Toda, and E. Yamao, Chem. Abstr., 70, 114968 (1970).
15. N. J. Leonard and E. W. Nommensen, J. Am. Chem. Soc., 71, 2808 (1949).
16. W. B. Lutz, S. Lazarus, and R. I. Meltzer, J. Org. Chem., 27, 1695 (1962).
17. M. Dagonneau, E. S. Kagan, V. I. Mikhailov, E. G. Rozantsev, and V. D. Sholle, Synthesis, 895 (1984).
18. M. Y. Fioshin, I. A. Avrutskaya, I.I. Surov, and V. T. Novikov, Collect. Czech. Chem. Commun., 52, 182 (1987).
19. G. M. Rosen, J. Med. Chem., 17, 358 (1974).
20. E. G. Rozantsev and Y. V. Kokhanov, Izv. Akad. Nauk USSR., Ser. Khim., 1422 (1966)
21. E. G. Rozantsev and Y. V. Kokhanov, Izv. Akad. Nauk USSR., Chem. Abstr., 66, 54758 (1967).
22. J. M. Bobbitt, J. Org. Chem., 63, 9367 (1998).
23. O. L. Lebedev and S. N. Kazamovskii, Zhur. Obshch. Khim., 30, 1631 (1960);
24. O. L. Lebedev and S. N. Kazamovskii, Chem. Abstr., 55, 7792 (1961).
25. E. G. Rozantsev and M. B. Neiman, Tetrahedron, 20, 131 (1964).
26. R. Briere, H. Lemaire, and A. Rassat, Bull. Soc. Chim. Fr., 32, 3273 (1965).
27. W. Schilf, L. Stefaniak, J. Skolimwski, and G. A. Webb, J. Mol. Struct., 407, 1 (1997).
28. L. O. Atovmyan, V. A. Golubev, N. I. Golovina, and G. A. Klitskaya, Izv. Akad. Nauk USSR., Ser. Khim., 16, 92 (1975);
29. L. O. Atovmyan, V. A. Golubev, N. I. Golovina, and G. A. Klitskaya, Izv. Akad. Nauk USSR., Chem. Abstr., 82, 163631 (1975).
30. Z. Ciunik, J. Mol. Struct., 412, 27 (1997).
31. G. Moad, E. Rizzardo, and D. H. Solomon, Tetrahedron Lett., 22, 1165 (1981).
32. T. Miyazawa, T. Endo, S. Shiihashi, and M. Okawara, J. Org. Chem., 50, 1332 (1985).
33. E. G. Rozantsev, V. A. Golubev, and M. B. Neiman, Izv. Akad. Nauk USSR., Ser. Khim., 379 (1965);
34. E. G. Rozantsev, V. A. Golubev, and M. B. Neiman, Izv. Akad. Nauk USSR., Chem. Abstr., 62, 82415 (1965).
35. V. A. Golubev, R. I. Zhdanov, V. M. Gida, and E. G. Rozantsev, Izv. Akad. Nauk USSR., Ser. Khim., 4, 768 (1971);
36. V. A. Golubev, R. I. Zhdanov, V. M. Gida, and E. G. Rozantsev, Izv. Akad. Nauk USSR., Chem. Abstr., 75, 63571 (1971).
37. R. I. Zhdanov, V. A. Golubev, and £. G. Rozantsev, Izv. Akad. Nauk USSR., Ser. Khim., 1, 188 (1970);
38. R. I. Zhdanov, V. A. Golubev, and £. G. Rozantsev, Izv. Akad. Nauk USSR., Chem. Abstr., 72, 111227 (1970).
39. J. M. Bobbitt, Chem. Eng. News, 77, 6 (1999).
40. V. A. Golubev, R. I. Zhadov, and E. G. Rozantsev, Izv. Akad. Nauk USSR., Ser. Khim., 1, 186 (1970);
41. V. A. Golubev, R. I. Zhadov, and E. G. Rozantsev, Izv. Akad. Nauk USSR., Chem. Abstr., 72, 111229 (1970).
42. M. F. Semmelhack, C. S. Chou, and D. A. Cortes, J. Am. Chem. Soc., 105, 4492 (1983).
43. M. F. Semmelhack and C. R. Schmid, J. Am. Chem. Soc., 105, 6732 (1983).
44. P. L. Anelli, S. banfi, F. Montanari, and S. Quici, J. Org. Chem., 54, 2970 (1989).
45. F. Melvin, A. McMeill, P. J. F. Henderson, and R. B. Herbert, Tetrahedron Lett., 40, 1201 (1999).
46. C. Bolm, A. S. Magnus, and J. P. Hildebrand, Chemistry Lett., 2, 1173 (2000).
47. P. L. Bragd, A. C. Besemer, and H. Van Bekkum, J. Mol. Catal., A 170, 35 (2001).
48. N. Merbouh, J. M. Bobbitt, and C. Brückner, J. Carbohydr. Chem., 21, 65 (2002).
49. R. A. Miller and R. S. Hoermer, Org. Lett., 5, 285 (2003).
50. S. D. Rychnovsky and R. Vaidyanathan, J. Org. Chem., 64, 310 (1999).
51. J. Einhorn, C. Einhorn, F. Ratajczak, and J. L. Pierre, J. Org. Chem., 61, 7452 (1996).
52. S. Weik, G. Nicholson, G. Jung, and J. Rademann, Angew. Chem., Int. Ed., 40, 1436 (2001).
53. T. Inokuchi, S. Matsumoto, T. Nishiyama, and S. Torii, J. Org. Chem., 55, 462 (1990).
54. T. Inokuchi, P. Liu, and S. Torii, Chemistry Lett., 1411 (1994).
55. M. Zhao, J. Li, E. Mano, Z. Song, D. M. Tsahen, E. J. J. Grabowski, and P. Reider, J. Org. Chem., 64, 2564 (1999).
56. M. Fabbrini, C. Galli, P. Gentili, and D. Macchitella, Tetrahedron Lett., 42, 7551 (2001).
57. G. Sourkouni-Argirusi and A. Kirshning, Org. Lett., 2, 3781 (2000).
58. A. de Mico, R. Margarita, L. Parlanti, A. Vesconi, and G. Piancatelli, J. Org. Chem., 62, 6974(1997).
59. J. B. Epp and T. S. Widlanski, J. Org. Chem., 64, 293 (1999).
60. T. Miyazawa and T. Endo, J. Mol. Catal., 31, 217 (1985).
61. T. Miyazawa and T. Endo, J. Mol. Catal., 32, 357 (1985).
62. M. F. Semmelhack, C. R. Schmid, D. A. Cortes, and C. S. Chou, J. Am. Chem. Soc., 106, 3374(1984).
63. S. S. Kim and K. Nehru, Synlett, 616 (2002).
64. R. Ben-Daniel, P. Alsters, and R. Neumann, J. Org. Chem., 66, 8650 (2001).
65. S. S. Kim and H. C. Jung, Synthesis, 2135 (2003).
66. A. Dijksman, I. W. C. E. Arends, and R. A. Sheldon, Chem. Commun., 1591 (1999).
67. A. Cecchetto, F. Fontana, F. Minisci, and F. Recupero, Tetrahedron Lett., 42, 6651 (2001).
68. I. A. Ansari and R. Gree, Org. Lett., 4, 1507 (2002).
69. S. Lemoine, C. Thomazeau, D. Joannard, S. Trombotto, G. Descotes, A. Bouchu, and Y. Queneau, Carbohydr. Res., 326, 176 (2000).
70. M. F. Semmelhack, C. R. Schmid, and D. A. Cortes, Tetrahedron Lett., 27, 1119 (1986).
71. S. Kishioka, S. Ohki, T. Ohsaka, and K. Tokuda, J. Electroanal. Chem., 452, 179 (1998).
72. P. L. Anelli, F. Montanari, and S. Quid, Org. Synth., 69, 212 (1990).
73. N. Merbouh, J. F. Thaburet, M. Ibert, F. Marsais, and J. M. Bobbitt, Carbohydr. Res., 336, 75 (2001).
74. N. J. Davis and S. L. Flitsch, Tetrahedron Lett., 34, 1181 (1993).
75. A. E. J. de Nooy, A. C. Besemer, and H. van Bekkum, Tetrahedron, 51, 8023 (1995).
76. A. E. J. de Nooy, A. C. Besemer, and H. van Bekkum, Carbohydr. Res., 269, 89 (1995).
77. J. F. Thaburet, N. Merbouh, M. Ibert, F. Marsais, and G. Queguiner, Carbohydr. Res., 330, 21 (2001).
78. J. A. Celia, J. A. Kelley, and E. F. Kenehan, J. Org. Chem., 40, 1860 (1975).
79. C. Palomo, J. M. Aizpurua, C. Cuevas, R. Urguechi, and A. Linden, J. Org. Chem., 61, 4400 (1996).
80. R. Siedlecka, J. Skarzewski, and J. Mlochowski, Tetrahedron. Lett., 31, 2177 (1990).
81. R. Siedlecka and J. Skarzewski, Synthesis, 401 (1994).
82. N. S. Cho and C. H. Park, Bull. Korean Chem. Soc., 15, 924 (1994);
83. N. S. Cho and C. H. Park, Chem. Abstr., 122, 105358 (1995).
84. E. Yoshida, K. Nakamura, T. Takata, and T. Endo, J. Polym. Sci., Part A: Polym. Chem., 31, 1505(1993).
85. W. Summerman and U. Deffner, Tetrahedron, 31, 593 (1975).
86. Y. Kashiwagi, Y. Yanagisawa, F. Kurashima, J. Anzai, T. Osa, and J. M. Bobbitt, Chem. Commun., 2745 (1996).
87. E. M. Belgsir and H. J. Schäfer, Chem. Commun., 435 (1999).
88. K. Schnatbaum and H. J. Schäfer, Synthesis, 5, 864 (1999).
89. E. M. Belgsir and H. J. Schäfer, Electrochem. Commun., 3, 32 (2001).
90. M. Schämann and H. J. Schäfer, Eur. J. Org. Chem., 351 (2003).
91. T. Osa, U. Akiba, I. Segawa, and J. M. Bobbitt, Chemistry Lett., 1423 (1988).
92. T. Osa, Y. Kashiwagi, K. Mukai, A. Ohsawa, and J. M. Bobbitt, Chemistry Lett., 75 (1990).
93. Y. Kashiwagi, A. Ohsawa, T. Osa, Z. Ma, and J. M. Bobbitt, Chemistry Lett., 581 (1991).
94. Y. Kashiwagi, F. Kurashima, C. Kikuchi, J. i. Anzai, T. Osa, and J. M. Bobbitt, Chem. Commun., 1983 (1999).
95. T. Osa, Y. Kashiwagi, Y. Yanagisawa, and J. M. Bobbitt, Chem. Commun., 2535 (1994).
96. Y. Kashiwagi, F. Kurashima, S. Chiba, J. Anzai, T. Osa, and J. M. Bobbitt, Chem. Commun., 114 (2003).
97. Z. Ma and J. M. Bobbitt, J. Org. Chem., 56, 6110 (1991).
98. C. A. Kemag, J. M. Bobbitt, and D. V. McGrath, Tetrahedron Lett., 40, 1635 (1999).
99. M. G. Banwell, M. P. Collis, M. F. Mackay, and S. L. Richards, J. Chem. Soc., Perkin Trans., 1, 1913 (1993).
100. M. G. Banwell, V. S. Bridges, J. R. Dupuche, S. L. Richards, and J. M. Walter, J. Org. Chem., 59, 6338 (1994).
101. N. Merbouh, J. M. Bobbitt, and C. Brückner, Tetrahedron Lett., 42, 8793 (2001).
102. M. Yamaguchi, T. Takata, and T. Endo, Tetrahedron Lett., 29, 5671 (1988).
103. M. Yamaguchi, T. Takata, and T. Endo, J. Org. Chem., 55, 1490 (1990).
104. T. Miyazawa and T. Endo, J. Org. Chem., 50, 3930 (1985).
105. T. Ren, Y. C. Liu, and Q. X. Guo, Bull. Chem. Soc. Jpn., 69, 2935 (1996).
106. Y. C. Liu, T. Ren, and Q. X. Guo, Chin. J. Chem., 14, 252 (1996);
107. Y. C. Liu, T. Ren, and Q. X. Guo, Chem. Abstr., 125, 300543 (1996).
108. V. A. Golubev, R. I. Zhdanov, I. T. Protsishin, and E. G. Rozantsev, Izv. Akad. Nauk USSR., Ser. Khim., 195, 952 (1970);
109. V. A. Golubev, R. I. Zhdanov, I. T. Protsishin, and E. G. Rozantsev, Izv. Akad. Nauk USSR., Chem. Abstr., 74, 76281 (1971).
110. V. A. Golubev and R. V. Miklyush, Zh. Org. Khim., 8, 1376 (1972).
111. T. Miyazawa and T. Endo, Tetrahedron Lett., 27, 3395 (1986).
112. J. M. Bobbitt, M. C. F. Guttermuth, Z. Ma, and H. Tang, Heterocycles, 30, 1131 (1990).
113. J. M. Bobbitt and Z. Ma, Heterocycles, 33, 641 (1992).
114. Y. B. Ding, I. Yang, Z. L. Liu, and Y. C. Liu, J. Chem. Res., Synop., 328 (1994).
115. Y. C. Liu, W. Wang, and Q. X. Guo, Chin. Chem. Lett., 7, 790 (1996);
116. Y. C. Liu, W. Wang, and Q. X. Guo, Chem. Abstr., 125, 328197 (1996).
117. Z. Ma, Ph.D Thesis, University of Connecticut (1991).
118. R. So, M. J. Mealy, and J. M. Bobbitt, University of Connecticut, unpublished results.
119. D. H. Hunter, D. H. R. Barton, and W. J. Motherwell, Tetrahedron Lett., 25, 603 (1984).
120. D. H. Hunter, J. S. Racok, A. W. Rey, and Y. Z. Ponce, J. Org. Chem., 53, 1278 (1988).
121. T. Takata, Y. Tsujino, S. Nakanishi, K. Nakamura, E. Yoshida, and T. Endo, Chemistry Lett., 937 (1999).
122. T. Kagiya, C. Komuro, K. Sakano, and S. Nishimoto, Chemistry Lett., 365 (1983).
123. B. Koop, A. Straub, and H. J. Schäfer, Tetrahedron: Asymmetry, 12, 341 (2001).
124. C. Harries, Justus Liebigs Arm. Chem., 417, 107 (1918).
125. T. Kawai, M. Jaijaoui, and R. L. Burwell Jr., J. Am. Chem. Soc., 104, 2951 (1982).
126. S. Baneijee and G. K. Trivedi, Tetrahedron, 48, 9939 (1992).
127. A. J. Ozinskas and A. M. Bobst, Helv. Chim. Acta, 63, 1407 (1980).
128. N. N. Quan and A. V. Guzzo, J. Phys. Chem., 85, 140 (1981).
129. V. A. Golubev, Y. E. Rashba, and A. N. Rozenberg, Izv. Akad. Nauk USSR., Ser. Khim., 12, 2442 (1982);
130. V. A. Golubev, Y. E. Rashba, and A. N. Rozenberg, Izv. Akad. Nauk USSR., Chem. Abstr., 98, 126015 (1983).