7 Nucleophilic Aromatic Substitution |
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285 |
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7 |
O− |
R |
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O2N |
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N+ |
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N 1′ |
R1 |
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N
NO2 R2
(35)
for reaction at the 1 -position of (35) relative to the 7-position increases with nitro substitution.62
Benzyne and Related Intermediates
It has been shown that, in the presence of lithium diethylamide at −70 ◦C, bromobenzoic acids form arynes which may react with arylacetonitriles to yield, predominantly, 2-cyanobenzoic acids.63 The reaction of alkyl and aryl isocyanides with benzyne may yield benzamide derivatives, showing their ability to act as charge-reversed equivalents to isocyanates.64 The generation and cyclization of a benzyne-tethered alkyllithium have been reported, and lead to a convenient synthetic route for 4-substituted indans.65
References
1Garcia-Meijide, M. C., Bravo-Diaz, C., and Romsted, L. S., Int. J. Chem. Kinet., 30, 31 (1998).
2Romsted, L. S., Zhang, J., and Zhuang, L., J. Am. Chem. Soc., 120, 10046 (1998).
3Baumgartner, M. T., Gallego, M. H., and Pierini, A. B., J. Org. Chem., 63, 6394 (1998).
4Crampton, M. R., and Holmes, A. J., J. Phys. Org. Chem., 11, 787 (1998).
5Forlani, L., Boga, C., Mazza, M., Cavrini, V., and Andrisano, V., Tetrahedron, 54, 4647 (1998).
6Crampton, M. R. and Robotham, I. A., Can. J. Chem., 76, 627 (1998).
7Persson, J. and Matsson, O., J. Org. Chem., 63, 9348 (1998).
8Loppinet-Serani, A., Charbonnier, F., Rolando, C., and Huc, I., J. Chem. Soc., Perkin Trans. 2, 1998, 937.
9Boga, C., Forlani, L., and Guardia, P., Gazz. Chim. Ital., 127, 259 (1997); Chem. Abs., 128, 12997 (1998).
10Jain, A. K., Sahoo, B. B., Atray, N., Jain, V., and Singh, P., J. Chem. Res. (S), 1998, 534.
11Jain, A. K., Kaushik, R. D., Singh, P., Sahoo, B. B., Atray, N., and Jain, V., Indian J. Chem., 36B, 1132 (1997); Chem. Abs., 128, 321287 (1998).
12Nudelman, N. S., Savidi, M., Nicotra, V., and Yankelevich, J., An. Asoc. Quim. Argent., 85, 231 (1997); Chem. Abs., 129, 67444 (1998).
13Wolff, J. J., Zietsch, A., Oeser, T., and Bolocan, J., J. Org. Chem., 63, 5164 (1998).
14Landini, D., Maia, A., Secci, P., Vlasov, V. M., and Os’kina, I., New J. Chem., 22, 71 (1998).
15Salmoria, G. V., Dall’Oglio, E., and Zucco, C., Tetrahedron Lett., 39, 2471 (1998).
16Robert, J., Anouti, M., and Paris, J., New. J. Chem., 21, 1187 (1997).
17Tabatskaya, A. A., Vyalkov, A. I., Morozov, S. V., and Vlasov, V. M., Russ. J. Org. Chem., 34, 1655 (1998).
18Tabatskaya, A. A., Beregovaya, I. V., and Vlasov, V. M., Russ. J. Org. Chem., 34, 861 (1998).
19Litvak, V. V., Organohalogen Compd., 31, 529 (1997); Chem. Abs., 128, 261007 (1998).
20Huffman, J. W., Wu, M.-J., and Lu, J., J. Org. Chem., 63, 4510 (1998).
21Makosza, M. and Kwast, A., J. Phys. Org. Chem., 11, 341 (1998).
22Makosza, M. and Nizmov, S., Org. Prep. Proced. Int., 29, 707 (1997); Chem. Abs., 128, 61329 (1998).
23Stalewski, J., Tetrahedron Lett., 39, 9523 (1998).
24Makosza, M. and Bialecki, M., J. Org. Chem., 63, 4878 (1998).
25Makosza, M. and Sienkiewicz, K., J. Org. Chem., 63, 4199 (1998).
286 |
Organic Reaction Mechanisms 1998 |
26Makosza, M. and Stalinski, K., Chemistry, 3, 2025 (1997).
27Makosza, M. and Stalinski, K., Tetrahedron Lett., 39, 3575 (1998).
28Makosza, M. and Stalinski, K., Tetrahedron, 54, 8797 (1998).
29Adam, W., Makosza, M., Stalinski, K., and Zhao, C.-G., J. Org. Chem., 63, 4390 (1998).
30Orlov, V. Yu., Kotov, A. D., Rusakov, A. I., Bystryakova, E. B., Kopeikin, V. V., and Mironov, G. S.,
Russ. J. Org. Chem., 34, 538 (1998).
31Ramana, D. V., and Kantharaj, E., Indian J. Chem., 36B, 776 (1997); Chem. Abs., 128, 167105 (1998).
32Tarasenko, E. A., Artamkina, G. A., Voevodskaya, T. I., Lukashev, N. V., and Beletskaya, I. P., Russ.
J.Org. Chem., 34, 1459 (1998).
33Ross, J. P., Couture, D., and Warkentin, J., Can. J. Chem., 75, 1331 (1997).
34Selva, M., Tundo, P., and Perosa, A., J. Org. Chem., 63, 3266 (1998).
35Vlasov, V. M., Russ. J. Org. Chem., 34, 1310 (1998).
36Bunton, C. A., Foroudian, H. J., Gillitt, N. D., and Whiddon, C. R., Can. J. Chem., 76, 946 (1998).
37Cervera, M. and Marquet, J., Can. J. Chem., 76, 966 (1998).
38Frolov, A. N., Russ. Org. Chem., 34, 139 (1998).
39El-Wetery, A. S., El-Azoney, K. M., and Raieh, M., J. Labelled Compd. Radiopharm., 39, 987 (1997); Chem. Abs., 128, 101924 (1998).
40Mandal, S. K. and Sarkar, A., J. Org. Chem., 63, 1901 (1998).
41Goryunov, L. I., Nikitin, Yu. M., and Shteingarts, V. D., Russ. J. Org. Chem., 34, 1646 (1998).
42Frost, C. G. and Mendonca, P., J. Chem. Soc., Perkin Trans. 1, 1998, 2615.
43Kamikawa, K., Sugimoto, S., and Uemura, M., J. Org. Chem., 63, 8407 (1998).
44Anderson, B. A., Bell, E. C., Ginah, F. O., Harn, N. K., Pagh, L. M., and Wepsiec, J. P., J. Org. Chem., 63, 8224 (1998).
45Consiglio, G., Frenna, V., Mezzina, E., Pizzolato, A., and Spinelli, D., J. Chem. Soc., Perkin Trans. 2, 1998, 325.
46Zhao, W. and Shine, H. J., Can. J. Chem., 76, 695 (1998).
47Chambers, R. D., Hall, C. W., Hutchinson, J., and Millar, R. W., J. Chem. Soc., Perkin Trans. 1, 1998, 1705.
48Bazyl, I. T., Kisil, S. P., Sharapko, A. E., Burgart, Ya. V., Saloutin, V. I., and Chupakhin, O. N., Russ.
J.Org. Chem., 34, 363 (1998).
49 Hermecz, I., Vasvari-Debreczy, L., Polanyi, B., Kereszturi, G., Balogh, M., Horvath, A., and Varkonyi, P., Heterocycles, 48, 1111 (1998); Chem. Abs., 129, 161238 (1998).
50Cuenca, A., Int. J. Chem. Kinet., 30, 777 (1998).
51Kaminski, Z. J., Paneth, P., and Rudzinski, J., J. Org. Chem., 63, 4248 (1998).
52Itoh, T., Matsuya, Y., Nagata, K., Miyazaki, M., Tsutsumi, N., and Ohsawa, A., J. Chem. Soc., Perkin Trans. 1, 1998, 1637.
53Rusinov, V. L. and Chupakhin, O. N., Russ. J. Org. Chem., 34, 297 (1998).
54Chupakhin, O. N., Kozhevnikov, V. N., Kozhevnikov, D. N., and Rusinov, V. L., Russ. J. Org. Chem., 34, 388 (1998).
55Rusinov, G. L., Beresnev, D. G., and Chupakhin, O. N., Russ. J. Org. Chem., 34, 423 (1998).
56Boga, C. and Forlani, L., J. Chem. Soc., Perkin Trans. 2, 1998, 2155.
57Hasegawa, Y., J. Chem. Soc., Perkin Trans. 2, 1998, 1561.
58Annandale, M. T. van Loon, G. W. and Buncel, E., Can. J. Chem., 76, 873 (1998).
59Blokhina, N. I., Atroshchenko, Yu. M., Gitis, S. S., Blokhin, I. V., Grudtsyn, Yu. D., Andrianov, V. F., and Kaminskii, A., Ya., Russ. J. Org. Chem., 34, 499 (1998).
60Terrier, F., Pouet, M.-J., Gzouli, K., Halle, J.-C., Outurquin, F., and Paulmier, C., Can. J. Chem., 76, 937 (1998).
61Terrier, F., Pouet, M.-J., Halle, J.-C., Kizilian, E., and Buncel, E., J. Phys. Org. Chem., 11, 707 (1998).
62Dust, J. M. and Manderville, R. A., Can. J. Chem., 76, 662 (1998).
63Wang, A., Maguire, J. A., and Biehl, E., J. Org. Chem., 63, 2451 (1998).
64Rigby, J. H. and Laurent, S., J. Org. Chem., 63, 6742 (1998).
65Bailey, W. F. and Longstaff, S. C., J. Org. Chem., 63, 432 (1998).