Developments in microwave-assisted organic chemistry

Australian Journal of Chemistry

Volumn 48, Issue 10, 1995, Pages 1665-1692

  Strauss, Christopher R ^a   Trainor, Robert W ^a  

^a CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84924213784     PISSN: 00049425     EISSN: 14450038     Source Type: Journal    
DOI: 10.1071/CH9951665     Document Type: Article

References (190)

1. Trost, B. M., and Fleming, I., ‘Comprehensive Organic Synthesis’ Vols 1-9 (Pergamon: New York 1991).
2. Anand, N., Bindra, J. S., and Ranganathan, S., ‘Art in Organic Synthesis’ (John Wiley: New York 1988).
3. Larock, R. C., ‘Comprehensive Organic Transformations’ (VCH: New York 1989).
4. Krieger, J., Dagani, R., and Illman, D., Chem. Eng. News, 1993, 71(12), 28-67.
5. Emsley, J., New Sci., 1988, 119(1638), 56.
6. Gedye, R., Smith, F., Westaway, K., Ali, H., Baldisera, L., Laberge, L., and Rousell, J., Tetrahedron Lett., 1986, 27, 279.
7. Giguere, R. J., Bray, T. L., Duncan, S. M., and Majetich, G., Tetrahedron Lett., 1986, 27, 4945.
8. Gedye, R. N., Smith, F. E., and Westaway, K. C., Can. J. Chem., 1988, 66, 17.
9. Mingos, D. M. P., and Baghurst, D. R., Chem. Soc. Rev., 1991, 20, 1.
10. Gedye, R., Smith, F., and Westaway, K., J. Microwave Power Electromagn. Energy, 1991, 26, 3.
11. Abramovitch, R. A., Org. Prep. Proced. Int., 1991, 23, 683.
12. Loupy, A., Bram, G., and Sansoulet, J., New J. Chem., 1992, 16, 233.
13. Giguere, R. J., Mater. Res. Soc. Symp. Proc., 1992, 269, 387.
14. Toma, §., Chem. Listy, 1993, 87, 627.
15. Loupy, A., Spectra Anal, 1993, 22(175), 33.
16. Whittaker, A. G., and Mingos, D. M. P., J. Microwave Power Electromagn. Energy, 1994, 29, 195.
17. Mingos, D. M. P., Chem. Ind. (London), 1994, 596.
18. Cabiewski, T., Faux, A. F., and Strauss, C. R., J. Org. Chem., 1994, 59, 3408, and references cited therein.
19. Raner, K. D., Strauss, C. R., Trainor, R. W., and Thorn, J. S., J. Org. Chem., 1995, 60, 2456.
20. Metaxis, A. C., and Meredith, R. J., ‘Industrial Microwave Heating’ (a) Ch. 1, pp. 1-4; Ch. 10, pp. 277-295; (b) for a glossary of terms see Appendix VIII; (c) Ch. 3, pp. 26-69; (d) p. 155; (e) pp. 53, 81 (Peregrinus: London 1988).
21. Kingston, H. M., and Jassie, L. B., ‘Introduction to Microwave Sample Preparation’ (a) Ch. 2, pp. 7-32; (b) Ch. 6, pp. 93-154; (c) Ch. 11, pp. 231-243 (Am. Chem. Soc.: Washington, DC, 1988).
22. Straathof, A. J. J., van Bekkum, H., and Kieboom, A. P. G., Reel Trav. Chim. Pays-Bas, 1988, 107, 647.
23. Vázquez-Tato, M. P., Synlett, 1993, 506.
24. Molina, A., Vaquero, J. J., García-Navio, J. L., and Alvarez-Builla, J., Tetrahedron Lett., 1993, 34, 2673.
25. Gutierrez, E., Loupy, A., Bram, G., and Ruiz-Hitzky, E., Tetrahedron Lett., 1989, 30, 945.
26. Bram, G., Loupy, A., and Majdoub, M., Synth. Commun., 1990, 20, 125.
27. Bram, G., Loupy, A., Majdoub, M., Gutierrez, E., and Ruiz-Hitzky, E., Tetrahedron, 1990, 46, 5167.
28. Bram, G., Loupy, A., Majdoub, M., and Petit, A., Chem. Ind. (London), 1991, 396.
29. Petit, A., Loupy, A., Maillard, M., Ph., and Momenteau, M., Synth. Commun., 1992, 22, 1137.
30. Loupy, A., Pigeon, P., Ramdani, M., and Jacquault, P., J. Chem. Res. (S), 1993, 36.
31. Barnier, J. P., Loupy, A., Pigeon, P., Ramdani, M., and Jacquault, P., J. Chem. Soc., Perkin Trans. 1, 1993, 397.
32. Loupy, A., and Thach, L. N., Synth. Commun., 1993, 23, 2571.
33. Loupy, A., Pigeon, P., Ramdani, M., and Jacquault, P., Synth. Commun., 1994, 24, 159.
34. Abenhaïm, D., Ngoc Son, C. P., Loupy, A., and Ba Hiep, N., Synth. Commun., 1994, 24, 1199.
35. Abenhaïm, D., Loupy, A., Mahieu, C., and Séméria, D., Synth. Commun., 1994, 24, 1809.
36. Abenhaïm, D., Diez-Barra, E., de la Hoz, A., Loupy, A., and Sánchez-Migallón, A., Heterocycles, 1994, 38, 793.
37. Diaz-Ortiz, A., Diez-Barra, E., de la Hoz, A., Loupy, A., Petit, A., and Sánchez, L., Heterocycles, 1994, 38, 785.
38. Csiba, M., Cleophax, J., Loupy, A., Malthête, J., and Gero, S. D., Tetrahedron Lett., 1993, 34, 1787.
39. Loupy, A., Petit, A., Ramdani, M., Yvanaeff, C., Majdoub, M. M., Labiad, B., and Villemin, D., Can. J. Chem., 1993, 71, 90.
40. Villemin, D., Labiad, B., and Loupy, A., Synth. Commun., 1993, 23, 419.
41. Ben Alloum, A., Labiad, B., and Villemin, D., J. Chem. Soc., Chem. Commun., 1989, 386.
42. Villemin, D., Labiad, B., and Ouhilai, Y., Chem. Ind. (London), 1989, 607.
43. Villemin, D., and Ben Alloum, A., Synth. Commun., 1990, 20, 925.
44. Villemin, D., Lalaoui, M., and Ben Alloum, A., Chem. Ind. (London), 1991, 176.
45. Villemin, D., and Ben Alloum, A., Synth. Commun., 1990, 20, 3325.
46. Villemin, D., and Labiad, B., Synth. Commun., 1990, 20, 3333.
47. Villemin, D., and Labiad, B., Synth. Commun., 1990, 20, 3207.
48. Villemin, D., and Labiad, B., Synth. Commun., 1990, 20, 3213.
49. Villemin, D., and Ben Alloum, A., Synth. Commun., 1991, 21, 63.
50. Villemin, D., Ben Alloum A., and Thibault-Starzyk, F., Synth. Commun., 1992, 22, 1359.
51. Villemin, D., and Labiad, B., Synth. Commun., 1992, 22, 2043.
52. Villemin, D., Martin, B., and Garrigues, B., Synth. Commun., 1993, 23, 2251.
53. Villemin, D., and Martin, B., J. Chem. Res. (S), 1994, 146.
54. Villemin, D., and Sauvaget, F., Synlett, 1994, 435.
55. Latouche, R., Texier-Boullet, F., and Hamelin, J., Tetrahedron Lett., 1991, 32, 1179.
56. Pilard, J.-F., Klein, B., Texier-Boullet, F., and Hamelin, J., Synlett, 1992, 219.
57. Texier-Boullet, F., Latouche, R., and Hamelin, J., Tetrahedron Lett., 1993, 34, 2123.
58. Rechsteiner, B., Texier-Boullet, F., and Hamelin, J., Tetrahedron Lett., 1993, 34, 5071.
59. Latouche, R., Texier-Boullet, F., and Hamelin, J., Bull. Soc. Chim. Fr., 1993, 130, 535.
60. Touaux, B., Klein, B., Texier-Boullet, F., and Hamelin, J., J. Chem. Res. (S), 1994, 116.
61. Abdallah-El Ayoubi, S., Texier-Boullet, F., and Hamelin, J., Synthesis, 1994, 258.
62. Alvarez, C., Delgado, F., García, O., Medina, S., and Márquez, C., Synth. Commun., 1991, 21, 619.
63. Delgado, F., Alvarez, C., García, O., Penieres, G., and Márquez, C., Synth. Commun., 1991, 21, 2137.
64. Delgado, F., Cano, A. C., Garcia, O., Alvarado, J., Velasco, L., Alvarez, C., and Rudler, H., Synth. Commun., 1992, 22, 2125.
65. García, O., Delgado, F., Cano, A. C., and Alvarez, C., Tetrahedron Lett., 1993, 34, 623.
66. Martínez, L. A., Garcia, O., Delgado, F., Alvarez, C., and Patiño, R., Tetrahedron Lett., 1993, 34, 5293.
67. Yuan, Y., Gao, D., and Jiang, Y., Synth. Commun., 1992, 22, 2117.
68. Wang, Y., and Jiang, Y., Synth. Commun., 1992, 22, 2287.
69. Yuan, Y., Jiang, Y., and Gao, D., Synth. Commun., 1992, 22, 3109.
70. Yuan, Y., Jiang, Y., Pang, J., Zhang, X., and Yang, C., Gazz. Chim. Ral., 1993, 123, 519.
71. Deng, R., Wang, Y., and Jiang, Y., Synth. Commun., 1994, 24, 111.
72. Deng, R., Wang, Y., and Jiang, Y., Synth. Commun., 1994, 24, 1917.
73. Ipaktschi, J., and Bruck, M., Chem. Ber., 1990, 123, 1591.
74. Ley, S. V., and Mynett, D. M., Synlett, 1993, 793.
75. Varma, R. S., Varma, M., and Chatterjee, A. K., J. Chem. Soc., Perkin Trans. 1, 1993, 999.
76. Varma, R. S., Lamture, J. B., and Varma, M., Tetrahedron Lett., 1993, 34, 3029.
77. Varma, R. S., Chatterjee, A. K., and Varma, M., Tetrahedron Lett., 1993, 34, 4603.
78. Varma, R. S., Chatterjee, A. K., and Varma, M., Tetrahedron Lett., 1993, 34, 3207.
79. Subbaraju, G. V., Manhas, M. S., and Bose, A. K., Tetrahedron Lett., 1991, 32, 4871.
80. Banik, B. K., Manhas, M. S., Kaluza, Z., Barakat, K. J., and Bose, A. K., Tetrahedron Lett., 1992, 33, 3603.
81. Bose, A. K., Manhas, M. S., Banik, B. K., and Robb, E. W., Res. Chem. Intermed., 1994, 20, 1.
82. Bose, A. K., Manhas, M. S., Ghosh, M., Shah, M., Raju, V. S., Bari, S. S., Newaz, S. N., Banik, B. K., Chaudhary, A. G., and Baraket, K. J., J. Org. Chem., 1991, 56, 6968.
83. Banik, B. K., Manhas, M. S., Newaz, S. N., and Bose, A. K., Bioorg. Med. Chem. Lett., 1993, 3, 2363.
84. Elder, J. W., J. Chem. Educ., 1994, 71, A142.
85. Bari, S. S., Bose, A. J., Chaudhary, A. G., Manhas, M. S., Raju, V. S., and Robb, E. W., J. Chem. Educ., 1992, 69, 928.
86. Srikrishna, A., and Nagaraju, S., J. Chem. Soc., Perkin Trans. 1, 1992, 311.
87. Gupta, R., Paul, S., Gupta, A. K., and Kachroo, P. L., Indian J. Chem., Sect. B, 1994, 33, 888.
88. Morcuende, A., Valverde, S., and Herradon, B., Synlett, 1994, 89.
89. Baghurst, D. R., and Mingos, D. M. P., J. Chem. Soc., Chem. Commun., 1992, 674.
90. Armstrong, B. F., and Neas, E. D., Sep. Sci. Technol., 1990, 25, 2007.
91. Gedye, R. N., Rank, W., and Westaway, K. C., Can. J. Chem., 1991, 69, 706.
92. Bond, G., Moyes, R. B., Pollington, S. D., and Whan, D. A., Chem. Ind. (London), 1991, 686.
93. Mingos, D. M. P., Res. Chem. Intermed., 1994, 20, 85.
94. Linders, J. T. M., Kokje, J. P., Overhand, M., Lie, T. S., and Maat, L., Reel Trav. Chim.Pays-Bas, 1988, 107, 449.
95. Baghurst, D. R., and Mingos, D. M. P., J. Organomet. Chem., 1990, 384, C57.
96. Woudenberg, R. H., Oosterhoff, B. E., Lie, T. S., and Maat, L., Reel Trav. Chim. Pays-Bas, 1992, 111, 119.
97. Linders, J. T. M., Briel, P., Fog, E., Lie, T. S., and Maat, L., Reel Trav. Chim. Pays-Bas, 1989, 108, 268.
98. Puciova, M., and Toma, S., Collect. Czech. Chem. Commun., 1992, 57, 2407.
99. Puciova, M., Ertl, P., and Toma, S., Collect. Czech. Chem. Commun., 1994, 59, 175.
100. Stuerga, D., Gonon, K., and Lallemant, M., Tetrahedron, 1993, 49, 6229.
101. Zhang, Y.-W., Shen, Z.-X., Pan, B., Lu, X.-H., and Chen, M.-H., Synth. Commun., 1995, 25, 857.
102. Matsumura-Inoue, T., Tanabe, M., Minami, T., and Ohashi, T., Chem. Lett., 1994, 2443.
103. Dabirmanesh, Q., and Roberts, R. M. G., J. Organomet. Chem., 1993, 460, C28.
104. Lie Ken Jie, M. S. F., and Yan-Kit, C., Lipids, 1988, 23, 367.
105. Khan, M. U., and Williams, J. P., Lipids, 1993, 28, 953.
106. Dasgupta, A., Banerjee, P., and Malik, S., Chem. Phys. Lipids, 1992, 62, 281.
107. Takano, S., Kijima, A., Sugihara, T., Satoh, S., and Ogasawa, K., Chem. Lett., 1989, 87.
108. Lei, B., and Fallis, A. G., J. Am. Chem. Soc., 1990, 112, 4609.
109. Lu, Y.-F., and Fallis, A. G., Tetrahedron Lett., 1993, 34, 3367.
110. Jones, G. B., and Chapman, B. J., J. Org. Chem., 1993, 58, 5558.
111. Jiang, Y., and Yuan, Y., Synth. Commun., 1994, 24, 1045.
112. Sowmya, S., and Balasubramanian, K. K., Synth. Commun., 1994, 24, 2097.
113. Kundu, M. K., Mukherjee, S. B., Balu, N., Padmakumar, R., and Bhat, S. V., Synlett, 1994, 444.
114. Chang, Y.-C., Nair, M. G., Santell, R. C., and Helferich, W. G., J. Agric. Food Chem., 1994, 42, 1869.
115. DuPont, registered trade name.
116. Ali, M., Bond, S. P., Mbogo, S. A., McWhinnie, W. R., and Watts, P. M., J. Organomet. Chem., 1989, 371, 11.
117. Baghurst, D. R., Cooper, S. R., Greene, D. L., Mingos, D. M. P., and Reynolds, S. M., Polyhedron, 1990, 9, 893.
118. Baghurst, D. R., Mingos, D. M. P., and Watson, M., J., J. Organomet. Chem., 1989, 368, C43.
119. Greene, D. L., and Mingos, D. M. P., Transition Met. Chem., 1991, 16, 71.
120. Abramovitch, R. A., and Bulman, A., Synlett, 1992, 795.
121. Adämek, F., and Hajek, M., Tetrahedron Lett., 1992, 33, 2039.
122. Baptistelia, L. H. B., Neto, A. Z., Onaga, H., and Godoi, E. A. M., Tetrahedron Lett., 1993, 34, 8407.
123. Gordon, E. M., Gaba, D. C., Jebber, K. A., and Zacharias, D. M., Organometallics, 1993, 12, 5020.
124. Majetich, G., and Hicks, R., J. Microwave Power Electromagn. Energy, 1995, 30, 27.
125. Hwang, D.-R., Moerlein, S. M., Lang, L., and Welch, M. J., J. Chem. Soc., Chem. Commun., 1987, 1799.
126. Stone-Elander, S., and Elander, N., Appl. Radiat. Isot., 1993, 44, 889, and references therein.
127. Stone-Elander, S. A., Elander, N., Thorell, J.-O., Solas, G., and Svennebrink, J., J. Labelled Compd. Radiopharm., 1994, 34, 949.
128. Zijlstra, S., de Groot, T. J., Kok, L. P., Visser, G. M., and Vaalburg, W., J. Org. Chem., 1993, 58, 1643.
129. Wan, J. K. S., Wolf, K., and Heyding, R. D., in ‘Catalysis on the Energy Scene’ (S. Kaliaguine and A. Mahay) pp. 561-568 (Elsevier: Amsterdam 1984).
130. Yat Tse, M., Depew, M. C., and Wan, J. K. S., Res. Chem. Intermed., 1990, 13, 221.
131. Wan, J. K. S., Bamwenda G., and Depew, M. C., Res. Chem. Intermed., 1991, 16, 241.
132. Dinesen, T. R. J., Tse, M. Y., Depew, M. C., and Wan, J. K. S., Res. Chem. Intermed., 1991, 15, 113.
133. Wolf, K., Choi, H. K. J., and Wan, J. K. S., AOSTRA J: Res., 1986, 3, 53.
134. Gilman, L., and Grooms, W., Anal. Chem., 1988, 60, 1624.
135. Pagnotta, M., Nolan, A., and Kim, L., J. Chem. Educ., 1992, 69, 599.
136. Pollington, S. D., Bond, G., Moyes, R. B., Whan, D. A., Candlin, J. P., and Jennings, J. R., J. Org. Chem., 1991, 56, 1313.
137. Matsumura-Inoue, T., Tanabe, M., Minami, T., and Ohashi, T., Chem. Lett., 1994, 2443.Plazl, I., Acta Chim. Slov., 1994, 41, 437.
138. Abramovitch, R. A., Abramovitch, D. A., Iyanar, K., and Tamareselvy, K., Tetrahedron Lett., 1991, 32, 5251. '
139. Baghurst, D. R., and Mingos, D. M. P., J. Chem. Soc., Dalton Trans., 1992, 1151.
140. Chen, S.-T., Chiou, S.-H., and Wang, K.-T., J. Chem. Soc., Chem. Commun., 1990, 807.
141. Pougnet, M. A. B., Schnautz, N. G., and Walker, A. M., S.-Afr. Tydskr. Chem., 1992, 45(4), 86.
142. Pougnet, M., Downing, B., and Michelson, S., J. Microwave Power Electromagn. Energy, 1993, 28, 113.
143. Stull, D. R., Ind. Eng. Chem., 1947, 39, 517.
144. Constable, D., Raner, K., Somlo, R, and Strauss, C., J. Microwave Power Electromagn. Energy, 1992, 26, 195.
145. Raner, K. D., and Strauss, C. R., J. Org. Chem., 1992, 57, 6231.
146. Raner, K. D., Strauss, C. R., Vyskoc, F., and Mokbel, L., J. Org. Chem., 1993, 58, 950.
147. Reid, H. J., Greenfield, S., and Edmonds, T. E., Analyst, 1993, 118, 443, and references therein.
148. Küsefoglu, S. H., Kress, A. O., and Mathias, L. J., Macromolecules, 1987, 20, 2326.
149. Ueda, M., Koyama, T., Mano, M., and Yazawa, M., J. Polym. Sei, Part A: Polym. Chem., 1989, 27, 751.
150. Mathias, L. J., Warren, R. M., and Huang, S., Macromolecules, 1991, 24, 2036.
151. Avci, D., and Küsefoglu, S. H., J. Polym. Sei., Part A: Polym. Chem., 1993, 31, 2941.
152. Avci, D., Küsefoglu, S. H., Thompson, R. D., and Mathias, L. J., Macromolecules, 1994, 24, 2036.
153. Kress, A. O., Mathias, L. J., and Cei, G., Macromolecules, 1989, 22, 537.
154. Strauss, C. R., Galbraith, M. N., and Faux, A. F., PCT Int. Appl. WO 9118861 (CSIRO) (1991) (Chem. Abstr., 1992, 116, 128185v).
155. Furniss, B. S., Hannaford, A. J., Rogers, V., Smith, P. W. G., and Tatchell, A. R., “Vogel’s Textbook of Practical Organic Chemistry” 4th Edn (Longman: New York 1978).
156. Bevan, C. D., and Marshall, P. S., Nat. Prod. Rep., 1994, 11, 451.
157. Renoll, M., and Newman, M. S., Org. Synth., 1955, Collect Vol. 3, 502.
158. Kontoghiorghes, G. J., Drugs Future, 1988, 13, 413.
159. Anon., Drugs Future, 1994, 19, 503.
160. Singh, S., Chem. Ind. (London), 1994, 452.
161. Kontoghiorghes, G. J., and Sheppard, L., Inorg. Chim. Acta, 1987, 136, Lll.
162. Blum, P. A., Ph.D. Thesis, Monash University, 1991.
163. Brown, E. V., Synthesis, 1958, 358.
164. Strauss, C. R., and Trainor, R. W., Org. Prep. Proced. Int., in press. Breslow, R., Acc. Chem. Res., 1991, 24, 159.
165. Grieco, P. A., Aldrichimica Acta, 1991, 24, 59.
166. Lubineau, A., Auge, J., and Queneau, Y., Synthesis, 1994, 741.
167. Grieco, P. A., Brandes, E. B., McCann, S., and Clark, J. D., J. Org. Chem., 1989, 54, 5849.
168. Li, C.-J., Chem. Rev., 1993, 93, 2023.
169. Blokzijl, W., and Engberts, J. B. F. N., Angew. Chem., Int. Ed. Engl, 1993, 32, 1545.
170. Sealock, L. J., Elliott, D. C., Baker, E. G., and Butner, R. S., Ind. Eng. Chem. Res., 1993, 32, 1535.
171. Siskin, M., and Katritzky, A. R., Science, 1991, 231.
172. Kirschner, E. M., Chem. Eng. News, 1994, 72(25), 13.
173. Illman, D. L., Chem. Eng. News, 1994, 72(36), 22.
174. Hughes, D. L., Org. Prep. Proced. Int., 1993, 25, 609.
175. Hügel, H. M., and Kennaway, D. J., Org. Prep. Proced. Int., 1995, 27, 3.
176. Fitzpatrick, J. T., and Hiser, R. D., J. Org. Chem,., 1957, 22, 1703.
177. Robinson, B., ‘The Fischer Indole Synthesis’ pp. 642, 653 (John Wiley: Chichester 1982).
178. Kraus, G. A., and Landgrebe, K., Synthesis, 1984, 885.
179. Carlson, R., Lundstedt, T., and Shabana, R., Acta Chem. Scand., Ser. B, 1986, 40, 534.
180. Sun, W. C., Guy, P. M., Jahngen, J. H., Rossomando, E. F., Jahngen, E. G. E., J. Org. Chem., 1988, 53, 4414.
181. Lewis, D. A., Summers, J. S., Ward, T. C., and McGrath, J. E., J. Polym. Sei., Part A: Polym. Chem., 1992, 30, 1647.
182. Bose, A. K., Manhas, M. S., Ghosh, M., Raju, V. S., Tabei, K., and Urbanczyk-Lipkowska, Z., Heterocycles, 1990, 30, 741.
183. Berlan, J., Giboreau, P., Lefeuvre, S., and Marchand, C., Tetrahedron Lett., 1991, 32, 2363.
184. Laurent, R., Laporterie, A., Dubac, J., Berlan, J., Lefeuvre, S., and Audhuy, M, J. Org. Chem., 1992, 57, 7099.
185. Jahngen, E. G. E., Lentz, R. R., Pesheck, P. S., and Sackett, P. H., J. Org. Chem., 1990, 55, 3406.
186. Schiffmann, R. F., in ‘Encyclopedia of Chemical Processing and Design’ (J. J. McKetta and W. A. Cunningham) Vol. 30, p. 220 (Marcel Dekker: New York 1989).
187. Leskovsek, S., Smidovnik, A., and Koloini, T., J. Org. Chem., 1994, 59, 7433.
188. Peterson, E. R., Proc. 28th Microwave Symp., p. 89 (International Microwave Power Institute: Manassas, Virginia, 1993).
189. Bose, A. K., Banik, B. K., and Manhas, M. S., Tetrahedron Lett., 1995, 36, 213.
190. Karmazsin, E., Barhoumi, R., and Satre, P., J. Therm. Anal., 1984, 29, 1269.