Hexadecyltributylphosphonium azide - A highly potent reagent for the synthesis of unusual azides

Synthesis

Volumn , Issue 22, 2007, Pages 3431-3446

  Banert, Klaus ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Azides; Nitrogen heterocycles; Rearrangements; Small ring compounds; Substitution reactions

Indexed keywords

AZIDES; NITROGEN HETEROCYCLES; REARRANGEMENTS; SMALL-RING COMPOUNDS;

CYCLOHEXANE; NITROGEN COMPOUNDS; SOLVENTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

AZIDE; HEXADECYLTRIBUTYLPHOSPHONIUM AZIDE; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; ISOLATION PROCEDURE; LIPOPHILICITY; METHODOLOGY; POLYMERIZATION; REVIEW; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 36749097331     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990854     Document Type: Review

References (211)

1. Reviews: (a) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. Int. Ed. 2005, 44, 5188;
2. Angew. Chem. 2005, 117, 5320.
3. (b) The Chemistry of Functional Groups Supplement D2: The Chemistry of Halides, Pseudo-Halides and Azides, Parts 1 and 2; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1995.
4. (c) Hassner, A. In Houben-Weyl, Vol. E16a, Part 2, 4th ed.; Klamann, D., Ed.; Thieme: Stuttgart, 1990, 1243.
5. (d) Scriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297.
6. (e) Benson, F. R. The High Nitrogen Compounds; Wiley: New York, 1984.
7. (f) Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic: Orlando (USA), 1984.
8. (g) The Chemistry of Functional Groups, Supplement D: The Chemistry of Halides, Pseudo-Halides and Azides; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1983.
9. (h) The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: London, 1971.
10. Abramovitch, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: London, 1971, 221.
11. (a) Schmidt, K. F. Angew. Chem. 1923, 36, 511.
12. (b) Schmidt, K. F. Ber. Dtsch. Chem. Ges. 1924, 57, 704.
13. (c) Krow, G. R. Tetrahedron 1981, 37, 1283.
14. (d) Pearson, W. H.; Hutta, D. A.; Fang, W. J. Org. Chem. 2000, 65, 8326.
15. (e) Pearson, W. H.; Fang, W. J. Org. Chem. 2000, 65, 7158.
16. Engel, A. In Houben-Weyl; Klamann, D., Ed.; Thieme: Stuttgart, 1990.
17. Sheradsky, T. In The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: London, 1971, 331.
18. (a) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
19. (b) Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437.
20. (c) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353.
21. (a) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565;
22. Angew. Chem. 1963, 75, 604.
23. (b) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry, Vol. 1; Padwa, A., Ed.; Wiley: New York, 1984, 1.
24. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596;
25. Angew. Chem. 2002, 114, 2708.
26. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
27. Reviews: (a) Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51.
28. (b) Lutz, J.-F. Angew. Chem. Int. Ed. 2007, 46, 1018;
29. Angew. Chem. 2007, 119, 1036.
30. Hemmer, R.; Lürken, W. In Houben-Weyl, Vol. E16d, Part 2, 4th ed.; Klamann, D., Ed.; Thieme: Stuttgart, 1992, 646.
31. Ferrier, R. J. Carbohydr. Chem. 2003, 34, 136.
32. Breslow, D. S. In Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic: Orlando (USA), 1984, 491.
33. (a) Hammerl, A.; Klapötke, T. M.; Rocha, R. Eur. J. Inorg. Chem. 2006, 2210.
34. (b) Dabbagh, H. A.; Lwowski, W. J. Org. Chem. 2000, 65, 7284.
35. (c) Kurz, D.; Reinhold, J. J. Mol. Struct. (Theochem) 1999, 492, 187.
36. (d) Cubero, E.; Orozco, M.; Luque, F. J. J. Org. Chem. 1998, 63, 2354.
37. (e) Henry, R. A.; Finnegan, W. G.; Lieber, E. J. Am. Chem. Soc. 1954, 76, 88.
38. Gagneux, A.; Winstein, S.; Young, W. G. J. Am. Chem. Soc. 1960, 82, 3766.
39. (a) L'abbé, G.; Hassner, A. Angew. Chem., Int. Ed. Engl. 1971, 10, 98;
40. Angew. Chem. 1971, 83, 103.
41. (b) Smolinsky, G.; Pryde, C. A. In The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: London, 1971, 555.
42. (c) Hassner, A. In Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic: Orlando (USA), 1984, 35.
43. (d) Banert, K. In Houben-Weyl, Vol. E15, 4th ed.; Kropf, H.; Schaumann, E., Eds.; Thieme: Stuttgart, 1993.
44. Lwowski, W. In The Chemistry of the Azido Group; Patai, S., Ed.; Wiley: London, 1971, 503.
45. (a) Nair, V. In The Chemistry of Heterocyclic Compounds, Small-Ring Heterocycles, Vol. 42, Part 1; Hassner, A., Ed.; Wiley: New York, 1983, 215.
46. (b) Backes, J. In Houben-Weyl, Vol. E16c, 4th ed.; Klamann, D., Ed.; Thieme: Stuttgart, 1992, 317.
47. Ohta, S.; Tsuno, N.; Nakamura, S.; Taguchi, N.; Yamashita, M.; Kawasaki, I.; Fujieda, M. Heterocycles 2000, 53, 1939.
48. (a) Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. J. Am. Chem. Soc. 1990, 112, 4011.
49. (b) Derrer, S.; Davies, J. E.; Holmes, A. B. J. Chem. Soc., Perkin Trans. 1 2000, 2943.
50. (c) Derrer, S.; Davies, J. E.; Holmes, A. B. J. Chem. Soc., Perkin Trans. 1 2000, 2957.
51. Smith, P. A. S. In Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic: Orlando (USA), 1984, 95.
52. Griess, P. Proc. R. Soc. London 1864, 13, 375.
53. (a) Anselme, J.-P.; Fischer, W. Tetrahedron 1969, 25, 855.
54. (b) Reed, J. O.; Lwowski, W. J. Org. Chem. 1971, 36, 2864.
55. (a) Nyffeler, P. T.; Liang, C.-H.; Koeller, K. M.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 10773.
56. (b) Liu, Q.; Tor, Y. Org. Lett. 2003, 5, 2571.
57. (c) Yan, R.-B.; Yang, F.; Wu, Y.; Zhang, L.-H.; Ye, X.-S. Tetrahedron Lett. 2005, 46, 8993.
58. (d) Beckmann, H. S. G.; Wittmann, V. Org. Lett. 2007, 9, 1.
59. (a) Kirschning, A.; Monenschein, H.; Schmeck, C. Angew. Chem. Int. Ed. 1999, 38, 2594;
60. Angew. Chem. 1999, 111, 272.
61. (b) Kirschning, A.; Jesberger, M.; Monenschein, H. Tetrahedron Lett. 1999, 40, 8999.
62. (c) Kirschning, A.; Hashem, M. A.; Monenschein, H.; Rose, L.; Scheming, K.-U. J. Org. Chem. 1999, 64, 6522.
63. Hassner, A. Acc. Chem. Res. 1971, 4, 9.
64. Banert, K.; Lehmann, J. In Modern Allene Chemistry; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004, 359.
65. (a) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959.
66. (b) Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Angew. Chem. Int. Ed. 2000, 39, 3635;
67. Angew. Chem. 2000, 112, 3781.
68. Nishiyama, K.; Oba, M.; Watanabe, A. Tetrahedron 1987, 43, 693.
69. (a) Chavan, S. P.; Subbarao, Y. T. Tetrahedron Lett. 1999, 40, 5073.
70. (b) Seeberger, P. H.; Roehrig, S.; Schell, P.; Wang, Y.; Christ, W. J. Carbohydr. Res. 2000, 328, 61.
71. (c) Nair, V.; George, T. G.; Sheeba, V.; Augustine, A.; Balagopal, L.; Nair, L. G. Synlett 2000, 1597.
72. (d) Nair, V.; Nair, L. G.; George, T. G.; Augustine, A. Tetrahedron 2000, 56, 7607.
73. (e) Griesbeck, A. G.; Lex, J.; Saygin, K. M.; Steinwascher, J. Chem. Commun. 2000, 2205.
74. (f) Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Tetrahedron Lett. 2002, 43, 1201.
75. For asymmetric synthesis of α-azido carboxylic acids and ketones, including nucleophilic substitution of α-halo precursors, see: (a) Evans, D. A.; Ellman, J. A.; Dorow, R. L. Tetrahedron Lett. 1987, 28, 1123.
76. (b) Enders, D.; Klein, D. Synlett 1999, 719.
77. Grundmann, C. In Houben-Weyl, Vol. 10/3, 4th ed.; Stroh, R., Ed.; Thieme: Stuttgart, 1965, 777.
78. Alvarez, S. C.; Alvarez, M. T. Synthesis 1997, 413.
79. Review: Narayan, S.; Fokin, V. V.; Sharpless, K. B. In Organic Reactions in Water; Lindström, U. M., Ed.; Blackwell Publishers: Oxford, 2007, 350.
80. (a) Lowry, T. H.; Richardson, K. S. Mechanismen und Theorie in der Organischen Chemie; Verlag Chemie: Weinheim, 1980, Chap. 4.
81. (b) Harris, J. M.; Raber, D. J.; Hall, R. E.; Schleyer, P. v.R. J. Am. Chem. Soc. 1970, 92, 5729.
82. (a) Landini, D.; Maia, A.; Montanari, F. J. Am. Chem. Soc. 1978, 100, 2796.
83. (b) Landini, D.; Maia, A.; Montanari, F. Nouv. J. Chim. 1979, 3, 575.
84. (c) Maia, A. Pure Appl. Chem. 1995, 67, 697.
85. (a) Landini, D.; Maia, A.; Montanari, F.; Rolla, F. J. Org. Chem. 1983, 48, 3774.
86. (b) Ando, T.; Kimura, T.; Yamataka, H. Adv. Chem. Ser. 1987, 215, 103.
87. Banert, K.; Kirmse, W. J. Am. Chem. Soc. 1982, 104, 3766.
88. Ohtani, N.; Murakawa, S.; Watanabe, K.; Tsuchimoto, D.; Sato, D. J. Chem. Soc., Perkin Trans. 2 2000, 1851.
89. (a) Landini, D.; Maia, A.; Montanari, F. J. Chem. Soc., Perkin Trans. 2 1983, 461.
90. (b) De Giorgi, M.; Landini, D.; Maia, A.; Penso, M. Synth. Commun. 1987, 17, 521.
91. Banert, K. Chem. Ber. 1985, 118, 1564.
92. Banert, K.; Lehmann, J.; Quast, H.; Meichsner, G.; Regnat, D.; Seiferling, B. J. Chem. Soc., Perkin Trans. 2 2002, 126.
93. Banert, K.; Joo, Y.-H.; Rüffer, T.; Walfort, B.; Lang, H. Angew. Chem. Int. Ed. 2007, 46, 1168;
94. Angew. Chem. 2007, 119, 1187.
95. Banert, K.; Joo, Y.-H. unpublished results.
96. Brückner, R. Reaktionsmechanismen; Elsevier Spektrum: Heidelberg, 2004, 70.
97. (a) Brown, H. C.; Krishnamurthy, S. J. Am. Chem. Soc. 1973, 95, 1669.
98. (b) Roberts, J. D.; Chambers, V. C. J. Am. Chem. Soc. 1951, 73, 5034.
99. (c) Streitwieser, A. Chem. Rev. 1956, 56, 571.
100. (d) Elias, H.; Krutzik, S. Chem. Ber. 1966, 99, 1026.
101. (e) Gounelle, Y.; Solgadi, D. Bull. Soc. Chim. Fr. 1973, 3019.
102. (f) Chang, W.-S.; Elias, H. Chem. Ber. 1970, 103, 842.
103. (a) Cristol, S. J.; Brindell, G. D. J. Am. Chem. Soc. 1954, 76, 5699.
104. (b) Nickon, A.; Hammons, J. H. J. Am. Chem. Soc. 1964, 86, 3322.
105. (c) Schaefer, J. P.; Weinberg, D. S. J. Org. Chem. 1965, 30, 2635.
106. (d) Schaefer, J. P.; Weinberg, D. S. J. Org. Chem. 1965, 30, 2639.
107. (e) Tanigawa, Y.; Kanamaru, H.; Murahashi, S.-I. Tetrahedron Lett. 1975, 4655.
108. (f) Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567.
109. (g) Fischer, W.; Grob, C. A.; von Sprecher, G. Helv. Chim. Acta 1980, 63, 806.
110. (a) Grob, C. A.; Lutz, E. Helv. Chim. Acta 1981, 64, 153.
111. (b) Brown, H. C. The Nonclassical Ion Problem; Plenum: New York, 1977, Chap. 8.
112. (c) Takeuchi, K.; Kato, Y.; Moriyama, T.; Okamoto, K. Chem. Lett. 1981, 935.
113. (a) Roberts, D. D.; Hendrickson, W. J. Org. Chem. 1969, 34, 2415.
114. (b) Nordlander, J. E.; Gruetzmacher, R. R.; Kelly, W. J.; Jindal, S. P. J. Am. Chem. Soc. 1974, 96, 181.
115. A critical view on nucleophilic solvent participation in solvolysis: Gajewski, J. J. J. Am. Chem. Soc. 2001, 123, 10877.
116. (a) Fry, J. L.; Lancelot, C. J.; Lam, L. K. M.; Harris, J. M.; Bingham, R. C.; Raber, D. J.; Hall, R. E.; Schleyer, P. v.R. J. Am. Chem. Soc. 1970, 92, 2538.
117. (b) Kevill, D. N.; Shen, B. W. J. Am. Chem. Soc. 1981, 103, 4515.
118. Nucleophilic substitution with partial inversion was obtained in the case of 4-bromoadamantan-2-ones: Snatzke, G.; Eckhardt, G. Chem. Ber. 1968, 101, 2010.
119. Banert, K.; Kurnianto, A. Chem. Ber. 1986, 119, 3826.
120. (a) Bone, J. A.; Whiting, M. C. Chem. Commun. 1970, 115.
121. (b) Lenoir, D.; Mison, P.; Hyson, E.; Schleyer, P. v.R.; Saunders, M.; Vogel, P.; Telkowski, L.A. J. Am. Chem. Soc. 1974, 96, 2157.
122. (c) Bone, J. A.; Pritt, J. R.; Whiting, M. C. J. Chem. Soc., Perkin Trans. 2 1975, 1447.
123. (d) Nordlander, J. E.; Haky, J. E. J. Am. Chem. Soc. 1981, 103, 1518.
124. (e) Cheung, C. K.; Tseng, L. T.; Lin, M.-H.; Srivastava, S.; le Noble, W. J. J. Am. Chem. Soc. 1986, 108, 1598.
125. (f) Lenoir, D. Chem. Ber. 1973, 106, 2366.
126. (g) Lenoir, D.; Hall, R. E.; Schleyer, P. v.R. J. Am. Chem. Soc. 1974, 96, 2138.
127. (h) Lenoir, D.; Raber, D. J.; Schleyer, P. v.R. J. Am. Chem. Soc. 1974, 96, 2149.
128. (i) Kovacevic, D.; Goričnik, B.; Majerski, Z. J. Org. Chem. 1978, 43, 4008.
129. (j) Brown, H. C. The Nonclassical Ion Problem; Plenum: New York, 1977, 281.
130. Faulkner, D.; McKervey, M. A.; Lenoir, D.; Senkler, C. A.; Schleyer, P. v.R. Tetrahedron Lett. 1973, 705.
131. Kirmse, W.; Streu, J. J. Org. Chem. 1985, 50, 4187.
132. Kirmse, W.; Kampmann, K.-H.; Zellmer, V. Chem. Ber. 1987, 120, 1301.
133. (a) Gillespie, P.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1971, 10, 503;
134. Angew. Chem. 1971, 83, 493.
135. (b) Stohrer, W.-D.; Schmieder, K. R. Chem. Ber. 1976, 109, 285.
136. (a) Woodward, R. B.; Hoffmann, R. J. Am. Chem. Soc. 1965, 87, 395.
137. (b) Schöllkopf, U. Angew. Chem., Int. Ed. Engl. 1968, 7, 588;
138. Angew. Chem. 1968, 80, 603.
139. (c) Schleyer, P. v.R.; Sliwinski, W. F.; Van Dine, G. W.; Schöllkopf, U.; Paust, J.; Fellenberger, K. J. Am. Chem. Soc. 1972, 94, 125.
140. Banert, K. Tetrahedron Lett. 1985, 26, 5261.
141. (a) Nicolaides, A.; Nakayama, T.; Yamazaki, K.; Tomioko, H.; Koseki, S.; Stracener, L. L.; McMahon, R. J. J. Am. Chem. Soc. 1999, 121, 10563.
142. (b) Banert, K. Angew. Chem., Int. Ed. Engl. 1987, 26, 879;
143. Angew. Chem. 1987, 99, 932.
144. (c) Banert, K. Chem. Ber. 1989, 122, 123.
145. (d) Pearce, D. S.; Lee, M.-S.; Moore, H. W. J. Org. Chem. 1974, 39, 1362.
146. (e) Pearce, D. S.; Locke, M. J.; Moore, H. W. J. Am. Chem. Soc. 1975, 97, 6181.
147. (f) VanAllan, J. A.; Priest, W. J.; Marshall, A. S.; Reynolds, G. A. J. Org. Chem. 1968, 33, 1100.
148. (g) Hall, J. H. J. Am. Chem. Soc. 1965, 87, 1147.
149. (h) Hall, J. H.; Patterson, E. J. Am. Chem. Soc. 1967, 89, 5856.
150. (i) Smolinsky, G.; Pryde, C. A. J. Org. Chem. 1968, 33, 2411.
151. Review: Banert, K. In Houben-Weyl, Vol. E15, 4th ed.; Kropf, H.; Schaumann, E., Eds.; Thieme: Stuttgart, 1993, 1344.
152. Hassner, A.; Isbister, R. J.; Friederang, A. Tetrahedron Lett. 1969, 2939.
153. Fotsing, J. R.; Hagedorn, M.; Banert, K. Tetrahedron 2005, 61, 8904.
154. Banert, K.; Hagedorn, M. unpublished results.
155. (a) Judge, R. H.; Moule, D. C.; Biernacki, A.; Benkel, M.; Ross, J. M.; Rustenburg, J. J. Mol. Spectrosc. 1986, 116, 364.
156. (b) Clouthier, D. J.; Moule, D. C. J. Am. Chem. Soc. 1987, 109, 6259.
157. (c) Bogey, M.; Destombes, J. L.; Vallee, Y.; Ripoll, J. L. Chem. Phys. Lett. 1988, 146, 227.
158. (d) Vallée, Y.; Ripoll, J.-L.; Lacombe, S.; Pfister-Guillouzo, G. J. Chem. Res., Synop. 1990, 40;
159. J. Chem. Res., Miniprint 1990, 401.
160. (e) Karolczak, J.; Clouthier, D. J.; Judge, R. H.; Moule, D. C. J. Mol. Spectrosc 1991, 147, 61.
161. (f) Clouthier, D. J.; Karolczak, J.; Rae, J.; Chan, W.-T.; Goddard, J. D.; Judge, R. H. J. Chem. Phys. 1992, 97, 1638.
162. (g) Lewis-Bevan, W.; Gaston, R. D.; Tyrrell, J.; Stork, W. D.; Salmon, G. L. J. Am. Chem. Soc. 1992, 114, 1933.
163. (h) Bogey, M.; Demuynck, C.; Destombes, J. L.; Vallee, Y.; Ripoll, J. L. J. Mol. Spectrosc. 1995, 172, 344.
164. (i) Born, M.; Ingemann, S.; Nibbering, N. M. M. J. Phys. Chem. 1996, 100, 17662.
165. (j) Tyndall, G. S.; Orlando, J. J.; Wallington, T. J.; Hurley, M. D. J. Phys. Chem. A 2001, 105, 5380.
166. These experiments were performed in collaboration with Dr. Hans Peter Reisenauer and Prof. Günther Maier at the Justus-Liebig-Universität Gießen.
167. Banert, K. Chem. Ber. 1989, 122, 1175.
168. Banert, K. Chem. Ber. 1989, 122, 1963.
169. Banert, K. Umlagerungen organischer Azide. Reaktionsmechanismen und Anwendungen in der Synthese; Schäuble Verlag: Rheinfelden, 1993.
170. (a) Huestis, L. D.; Andrews, L. J. J. Am. Chem. Soc. 1961, 83, 1963.
171. (b) White, W. N.; Norcross, B. E. J. Am. Chem. Soc. 1961, 83, 1968.
172. Banert, K. Angew. Chem., Int. Ed. Engl. 1985, 24, 216;
173. Angew. Chem. 1985, 97, 231.
174. Banert, K.; Kuhtz, A. unpublished results.
175. (a) L'abbé, G.; Mahy, M.; Bollyn, M.; Germain, G.; Scheefer, G. Bull. Soc. Chim. Belg. 1983, 92, 881.
176. (b) L'abbé, G. Bull. Soc. Chim. Belg. 1984, 93, 579.
177. (c) Hassner, A.; Keogh, J. J. Org. Chem. 1986, 51, 2767.
178. Shiner, V. J. Jr.; Humphrey, J. S. Jr. J. Am. Chem. Soc. 1967, 89, 622.
179. Banert, K. Chem. Ber. 1989, 122, 911.
180. Baldwin, M. G.; Johnson, K. E.; Lovinger, J. A.; Parker, C. O. J. Polym. Sci., Part B 1967, 5, 803.
181. Banert, K.; Hagedorn, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1675;
182. Angew. Chem. 1989, 101, 1710.
183. (a) Banert, K.; Hagedorn, M. Angew. Chem., Int. Ed. Engl. 1990, 29, 103;
184. Angew. Chem. 1990, 102, 90.
185. (b) Banert, K.; Hagedorn, M.; Knözinger, E.; Becker, A.; Würthwein, E.-U. J. Am. Chem. Soc. 1994, 116, 60.
186. Reviews on the synthesis of 1,2,3-triazoles: (a) Krivopalov, V. P.; Shkurko, O. P. Russ. Chem. Rev. 2005, 74, 339.
187. (b) Dehne, H. In Houben-Weyl, Vol. E8d, 4th ed.; Schaumann, E., Ed.; Thieme: Stuttgart, 1994, 305.
188. (c) Tomé, A. C. In Science of Synthesis, Vol. 13, 5th ed.; Storr, R. C.; Gilchrist, T. L., Eds.; Thieme: Stuttgart, 2004, 415.
189. (a) Banert, K. Liebigs Ann./Recl. 1997, 2005.
190. (b) Banert, K. Targets in Heterocyclic Systems 2000, 3, 1.
191. (a) Harrison, T.; Owens, A. P.; Williams, B. J.; Swain, C. J.; Williams, A.; Carlson, E. J.; Rycroft, W.; Tattersall, F. D.; Cascieri, M. A.; Chicchi, G. G.; Sadowski, S.; Rupniak, N. M. J.; Hargreaves, R. J. J. Med. Chem. 2001, 44, 4296.
192. (b) Owens, A. P. (Merck Sharp and Dohme Ltd) WO 9629317, 1996; Chem. Abstr. 1997, 126: 8122.
193. (c) Baker, R.; Elliot, J.; Stevenson, G. I.; Swain, C. J. (Merck Sharp & Dohme Ltd) WO 9701553, 1997; Chem. Abstr. 1997, 126: 171610.
194. (d) Baker, R.; Elliot, J.; Stevenson, G. i.; Swain, C. J. (Merck Sharp & Dohme Ltd) WO 9701554, 1997; Chem. Abstr. 1997, 126: 171611.
195. (e) Moseley, J. D.; Swain, C. J.; Williams, B. J. (Merck Sharp & Dohme Ltd) GB 2302689, 1997; Chem. Abstr. 1997, 126: 277501.
196. Loren, J. C.; Sharpless, K. B. Synthesis 2005, 1514.
197. Fotsing, J. R.; Banert, K. Eur. J. Org. Chem. 2005, 3704.
198. Priebe, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 736;
199. Angew. Chem. 1984, 96, 728.
200. Banert, K. Chem. Ber. 1987, 120, 1891.
201. Summaries on the chemistry of bicycloprop-2-enyls: (a) Padwa, A.; Goldstein, S. I.; Rosenthal, R. J. J. Org. Chem. 1987, 52, 3278.
202. (b) Bickelhaupt, F.; de Wolf, W. H. Recl. Trav. Chim. Pays-Bas 1988, 107, 459.
203. (a) Padwa, A.; Blacklock, T. J.; Carlsen, P. H. J.; Pulwer, M. J. Org. Chem. 1979, 44, 3281.
204. (b) Padwa, A.; Smolanow, J.; Tremper, A. J. Org. Chem. 1976, 41, 543.
205. Gallagher, T. C.; Storr, R. C. Tetrahedron Lett. 1981, 22, 2905.
206. Hassner, A.; Keogh, J. Tetrahedron Lett. 1975, 1575.
207. (a) Banert, K.; Köhler, F. Angew. Chem. Int. Ed. 2001, 40, 174;
208. Angew. Chem. 2001, 113, 173.
209. (b) Banert, K.; Grimme, S.; Herges, R.; Heß, K.; Köhler, F.; Mück-Lichtenfeld, C.; Würthwein, E.-U. Chem. Eur. J. 2006, 12, 7467.
210. Kirmse, W.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 7989.
211. Banert, K.; Hagedorn, M.; Müller, A. Eur. J. Org. Chem. 2001, 1089.