Abstract
The effect of the properties of heteroaromatic compounds as acids and bases on their behavior in electrophilic substitution reactions was examined. The established peculiarities were compared with the behavior of functional compounds of the benzene series. The specific characteristics of the mechanisms of electrophilic substitution in the heteroaromatic series due to the acidic and basic properties of the heteroaromatic compounds are discussed.
Similar content being viewed by others
Literature cited
L. S. Efros and M. V. Gorelik, The Chemistry and Technology of Intermediates [in Russian], Khimiya, Moscow (1980), Chaps. 1–6.
Kh. Khinei, in: General Organic Chemistry [Russian translation], Vol. 1, Khimiya, Moscow (1981), p. 314.
A. F. Pozharskii, Theoretical Foundations of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).
M. N. Nach and J. F. Bunnett, J. Amer. Chem. Soc.,96, 936 (1974).
V. Calo, L. Lopez, G. Pesce, and P. E. Todesco, J. Chem. Soc., Perkin 2, No. 10, 1192 (1974).
D. E. Pearson and E. Buehler, Synthesis, No. 5, 455 (1971).
V. V. Ershov, G. A. Nikiforov, and A. A. Volod'kin, Sterically Hindered Phenols [in Russian], Khimiya, Moscow (1972).
P. F. Ranken and A. G. McKinie, Synthesis, No. 2, 117 (1984).
R. C. Cambie, P. S. Rutledge, T. Smith-Palmer, and P. D. Woodgate, J. Chem. Soc., Perkin 1, No. 11, 1161 (1976).
Y. Ogata, M. Kimura, Y. Kondo, H. Katoh, and Che-Fa-Ching, J. Chem. Soc., Perkin 2, No. 3, 451 (1984).
P. Haberfield and D. Paul, J. Amer. Chem. Soc.,87, 5502 (1965).
D. H. Hey, J. A. Leonard, and C. W. Rees, J. Chem. Soc., No. 11, 4579 (1962).
A. Guy, M. Lemaire, and J.-P. Guette, Chem. Commun., No. 1, 8 (1980).
A. Guy, M. Lemaire, and J.-P. Guette, Tetrahedron,38, 2339 (1982).
H. Pervez, L. Rees, and C. J. Suckling, Chem. Commun., No. 8, 512 (1985).
B. R. Suthers, P. H. Riggins, and D. E. Pearson, J. Org. Chem.,27, 447 (1962).
J. H. Gorvin, J. Chem. Soc., No. 4, 1237 (1953).
Organic Syntheses [Russian translation], Vol. 4, Izd. Inostr. Lit., Moscow (1953), p. 374.
Z. Vrba and Z. J. Allan, Tetrahedron Lett., No. 43, 4507 (1968).
B. M. Lynch, C. M. Chen, and Y. Y. Wigfield, Can. J. Chem.,46, 1141 (1968).
P. H. Griffiths, W. A. Walkey, and H. B. Watson, J. Chem. Soc., No. 5, 631 (1934).
K. Halvarsson and L. Melander, Arkiv Kemi,11, 77 (1957).
R. O. C. Norman and G. H. Radda, J. Chem. Soc., No. 7, 3030 (1961).
R. O. C. Norman and G. H. Radda, Proc. Chem. Soc., No. 12, 423 (1960).
Organic Syntheses [Russian translation], Vol. 2, Izd. Inostr. Lit., Moscow (1949), p. 116.
L. I. Belen'kii, Yu. B. Vol'kenshtein, and I. B. Karmanova, Usp. Khim.,46, 1698 (1977).
Organic Syntheses [Russian translation], Vol. 1, Izd. Inostr. Lit., Moscow (1949), p. 475.
D. E. Pearson and H. W. Pope, J. Org. Chem., 21, 381 (1956).
D. E. Pearson, H. W. Pope, W. N. Hargrowe, and W. E. Stamper, J. Org. Chem.,23, 1412 (1958).
L. I. Belen'kii, G. P. Gronova, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 951 (1971).
D. H. Derbishire and W. A. Waters, J. Chem. Soc., No. 2, 564 (1950).
Ya. L. Gol'dfarb, É. I. Novikova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2822 (1971).
Ya. L. Gol'dfarb and Yu. B. Vol'kenshtein, Zh. Obshch. Khim.,31. 616 (1961).
L. I. Belen'kii, I. B. Karmanova, and Ya. L. Gol'dfarb, Zh. Org. Khim.,9, 1514 (1973).
Ya. L. Gol'dfarb, I. B. Karmanova, Yu. B. Vol'kenshtein, and L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 11, 1474 (1978).
J.-P. Gesson, J.-C. Jacquesy, M.-P. Jouannetaud, and G. Morellet, Tetrahedron Lett.,24, 3095 (1983).
V. N. Belov, L. A. Kheifits, and S. I. Virezuh, Reactions and Methods for the Investigation of Organic Compounds [in Russian], Book 10, Goskhimizdat, Moscow (1961), p. 7.
B. P. Susz and J. Cook, Helv, Chim. Acta,37, 1273 (1954).
K. B. Starowiejski, S. Pasynkiewicz, A. Sporzynski, and A. Chowojnowski, J. Organomet. Chem., 94, 361 (1975).
L. I. Belen'kii, E. N. Gur'yanova, V. Knoppova, E. D. Lubuzh, I. P. Romm, and R. R. Shifrina, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 48 (1980).
L. I. Belen'kii, I. B. Karmanova, G. P. Gromova, É. I. Novikova, Ya. L. Gol'dfarb, V. S. Bogdanov, and L. V. Shmelev, Zh. Org. Khim.,9, 1499 (1973).
L. I. Belen'kii, V. S. Bogdanov, and I. B. Karmanova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1735 (1979).
I. P. Romm, L. I. Belen'kii, E. N. Gur'yanova, and Yu. K. Tovbin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2478 (1979).
J.-C. Jacquesi, M.-P. Jounnetaud, and S. Makani, Chem. Commun., No. 3, 110 (1980).
J. M. Brittain, P. B. D. de la Mare, and P. A. Newman, Tetrahedron Lett., No. 21, 4111 (1980).
F. Effenberger and P. Menzel, Angew. Chem.,83, 535 (1971).
G. A. Olah, J. A. Olah, and T. Ohyama, J. Amer. Chem. Soc.,106, 5284 (1984).
E. Ochiai, J. Pharm. Soc. Japan,60, 164 (1940); Chem. Abstr.,34, 5450 (1940).
German Patent No. 433100; Beilstein,26, Suppl. 2, 16 (1954).
A. E. A. Porter, in: General Organic Chemistry [Russian translation], Vol. 8, Khimiya, Moscow (1985), p. 190.
A. K. Sheinkman, S. I. Suminov, and A. N. Kost, Usp. Khim.,42, 1415 (1973).
A. K. Sheinkman, Khim. Geterotsikl. Soedin., No. 1, p. 3 (1974).
M. Hamana, Khim. Geterotsikl. Soedin., No. 9, 1155 (1973).
W. P. K. Girke, Tetrahedron Lett., No. 39, 3537 (1976).
W. P. K. Girke, Chem. Ber.,112, 1 (1979).
W. P. K. Girke, Chem. Ber.,112. 1348 (1979).
A. Kreutzberger, Angew. Chem.,79, 978 (1967).
S. V. Krivun, Dokl. Akad. Nauk SSSR,180, 615 (1968).
F. Krönnke and K. Dicnore, Chem. Ber.,92. 46 (1959).
R. Wizinger and H. Angeliner, Helv. Chim. Acta,49, 2046 (1966).
M. P. Carmody, M. J. Cook, N. L. Dassanayake, A. R. Katritzky, P. Linda, and R. D. Tack, Tetrahedron,32, 1767 (1976).
Ya. L. Gol'dfarb, E. I. Novikova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6 1233 (1971).
A. Albert, in: Physical Methods in the Chemistry of Heterocyclic Compounds [Russian translation], Khimiya, Moscow-Leningrad (1966), pp. 15–124.
A. R. Katritzky and C. D. Johnson, Angew. Chem.,79, 629 (1967).
S. Clementi, P. P. Forsythe, C. D. Johnson, A. R. Katritzky, and B. Terem, J. Chem. Soc., Perkin 2, No. 4, 399 (1974).
A. El-Anani, J. Banger, G. Bianchi, S. Clementi, C. D. Johnson, and A. R. Katritzky, J. Chem. Soc., Perkin 2, No. 7, 1065 (1973).
S. Clementi, P. P. Forsythe, C. D. Johnson, and A. R. Katritzky, J. Chem. Soc., Perkin 2, No. 12, 1675 (1973).
A. R. Katritzky, B. Terem, E. V. Scriver, S. Clementi, and H. O. Tarhan, J. Chem. Soc., Perkin 2, No. 14, 1600 (1975).
A. R. Katritzky, S. Clementi, and H. O. Tarhan, J. Chem. Soc., Perkin 2, No. 14, 1624 (1975).
A. R. Katritzky, C. Ogretir, H. O. Tarhan, H. M. Dou, and J. V. Metzger, J. Chem. Soc., Perkin 2, No. 14, 1614 (1975).
A. R. Katritzky, H. O. Tarhan, and B. Terem, J. Chem. Soc., Perkin 2, No. 14, 1620 (1975).
A. R. Katritzky, S. Clementi, G. Milletti, and G. V. Sebastiani, J. Chem. Soc., Perkin 2, No. 6, 613 (1978).
D. S. Noyce, J. A. Virgilio, and B. Bartman, J. Org. Chem.,38, 2657 (1973).
D. S. Noyce and S. A. Fike, J. Org. Chem.,38, 3316 (1973).
D. S. Noyce and G. T. Stowe, J. Org. Chem.,38, 3762 (1973).
D. S. Noyce and B. B. Sandel, J. Org. Chem.,40, 3762 (1975).
D. S. Noyce and G. V. Kaiser, J. Org. Chem.,34, 1008 (1969).
D. S. Noyce and H. J. Pavez, J. Org. Chem.,37, 2620, 2623 (1972).
D. S. Noyce, C. A. Lipinski, and R. W. Nichols, J. Org. Chem.,37, 2615 (1972).
D. S. Noyce, C. A. Lipinski, and G. M. Loudon, J. Org. Chem.,35, 1718 (1970).
D. S. Noyce and B. B. Sandel, J. Org. Chem.,41, 3640 (1976).
E. A. Hill, M. L. Gross, M. Stasiewicz, and M. Manion, J. Amer. Chem. Soc.,91, 7381 (1969).
T. J. Broxton, G. L. Butt, L. W. Deady, S. H. Toh, R. D. Topsom, A. Fischer, and M. W. Morgan, Can. J. Chem.,51, 1620 (1973).
G. T. Bruce, A. R. Cooksey, and K. J. Morgan, J. Chem. Soc., Perkin 2, No. 6, 551 (1975).
R. J. Abraham, E. Bullock and S. S. Mitra, Can. J. Chem.,37, 1859 (1959).
E. B. Whipple, Y. Chiang, and R. L. Hinman, J. Amer. Chem. Soc.,85, 26 (1963).
Y. Chiang and E. B. Whipple, J. Amer. Chem. Soc.,85, 2763 (1963).
R. Kassner, E. Krumtholz, and F. W. Stenber, Ann., No. 5, 789 (1981).
H. Hogeween, Rec. Trav. Chim.,85, 1072 (1966).
H. Hogeween, R. M. Kellogg, and K. A. Kuindersma, Tetrahedron Lett., No. 40, 3929 (1973).
L. I. Belen'kii, A. P. Yakubov, and Ya. L. Gol'dfarb, Zh. Org. Khim.,11, 424 (1975).
A. P. Yakubov, N. V. Grigor'eva, and L. I. Belen'skii, Zh. Org. Khim., 14, 641 (1978).
Ya. L. Gol'dfarb, M. A. Kalik, N. A. Shul'ts, and L. I. Belen'kii, Zh. Org. Khim.,15, 1289 (1979).
L. I. Belen'kii and A. P. Yakubov, Tetrahedron,40, 2471 (1984).
L. I. Belen'kii and A. P. Yakubov, Tetrahedron,42, 759 (1986).
U. E. Wiersum and H. Wynberg, Tetrahedron Lett., No. 31, 2951 (1967).
D. M. Brower and J. A. van Doorn, Rec. Trav. Chim.,89. 553 (1970).
D. M. Brower, J. A. van Doorn, and A. A. Kiffen, Rec. Trav. Chim.,91, 1359 (1972).
V. G. Kul'nevich and Yu. M. Shapiro, Khim. Geterotsikl. Soedin., No. 12, 1594 (1972).
L. I. Belen'kii, Khim. Geterotsikl, Soedin., No. 12, 1587 (1980).
V. Veinmayr, J. Amer. Chem. Soc.,72, 918 (1950).
L. I. Belen'kii, A. P. Yakubov, and I. A. Bessonova, Zh. Org. Khim.,13, 364 (1977).
L. I. Belen'kii and N. V. Grigor'eva, in: Topics in the Chemistry of Heterocyclic Compounds, edited by J. Kovac, Bratislava (1981), p. 121.
Ya. L. Gol'dfarb, A. A. Dudinov, and V. P. Litvinov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 1323 (1982).
Y. Yokoyama, Y. Yamashita, K. Takahashi, and T. Sone, Chem. Lett., No. 6, 813 (1981).
Y. Yokoyama, Y. Yamashita, K. Takahashi, and T. Sone, Bull. Chem. Soc. Japan,56, 2208 (1983).
Y. Yamashita, A. Yoshino, K. Takahashi, and T. Sone, The 46th National Meeting of the Chemical Society of Japan, Niigata, Oct. 1982, Abstr. 4P15; Y. Yamashita, H. Kobayashi, A. Yoshino, K. Takahashi, and T. Sone, Bull. Chem. Soc. Japan,57, 1312 (1984).
G. G. Furin and G. G. Yakobson, Izv. Sibirsk. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, Vol. 1, No. 2, 109 (1977).
M. Eckert-Maksic, J. Org. Chem.,45, 3355 (1980).
G. V. Boyd and K. Heatherington, J. Chem. Soc., Perkin 1, No. 21, 2523 (1973).
C. T. Wie, S. Sunder, and C. D. Bolaniou, Tetrahedron Lett., No. 44, 4605 (1968).
G. A. Olah, K. Dunne, D. P. Kelly, and Y. K. Mo, J. Amer. Chem. Soc.,94, 7438 (1972).
H. J. Chen, L. E. Hakka, R. L. Hinman, A. J. Kresge, and E. B. Whipple, J, Amer. Chem. Soc.,93, 5102 (1971).
T. Yamaoka, H. Hosoya, and S. Nagakura, Tetrahedron,24, 6203 (1968).
F. Effenberger and R. Niess, Angew, Chem.,79, 1100 (1967).
A. P. Yakubov, L. I. Belen'kii, and Ya. L. Gol'dfarb, Zh. Org. Khim.,7, 525 (1971).
T. A. Melent'eva, T. M. Filippova, L. V. Kazanskaya, I. M. Kustanovich, and V. M. Berezovskii, Zh. Obshch. Khim.,41, 179 (1971).
M. I. Struchkova, G. G. Dvoryantseva, N. P. Kostyuchenko, Yu. N. Sheinker, Yu. E. Sklyar, and R. P. Evstigneeva, Khim. Geterotsikl. Soedin., No. 3, 336 (1972).
Ya. L. Gol'dfarb, Yu. B. Vol'kenshtein (Volkenstein), and L. I. Belen'kii (Belen'kij), Angew. Chem.,80, 547 (1968).
L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 344 (1975).
Ya. L. Gol'dfarb (editor), New Directions in the Chemistry of Thiophene [in Russian], Nauka, Moscow (1976).
H. J. Anderson and C. E. Loader, Synthesis, No. 4, 353 (1985).
L. I. Belen'kii, G. P. Gromova, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1228 (1971).
Ya. L. Gol'dfarb, G. P. Gromova, and L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2275 (1974).
L. I. Belen'kii, Ya. L. Gol'dfarb, and G. P. Gromova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2733 (1973).
Ya. L. Gol'dfarb and Yu. B. Vol'kenshtein, Dokl. Akad. Nauk SSSR,128, 536 (1959).
Ya. L. Gol'dfarb, A. P. Yakubov, and L. I. Belen'kii, Dokl. Akad. Nauk SSSR,185, 941 (1969).
L. I. Belen'kii, I. B. Karmanova, and Ya. L. Gol'dfarb, Zh. Org. Khim.,7, 1743 (1971).
L. I. Belen'kii, E. I. Novikova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., No. 9, 1353 (1971).
L. I. Belen'kii, G. P. Gromova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., No. 5, 597 (1972).
Zh. I. Aksel'rod and V. M. Berezovskii, Usp. Khim.,39, 1337 (1970).
H. Saito and M. Hamana, Heterocycles,12, 475 (1979).
D. E. Pearson, W. W. Hargrowe, K. T. Judith, and B. R. Suhters, J. Org. Chem.,26, 789 (1961).
R. E. Lokhov, S. S. Lokhova, N. M. Gaidarova, and L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 9, 1236 (1981).
H. J. den Hertog, L. van der Does, and C. A. Landheer, Rec. Trav. Chim.,81, 864 (1962).
L. van der Does and H. J. den Hertog, Rec. Trav. Chim.,84, 951 (1965).
J. Abblard, C. Decoret, L. Cronenberg, and H. Pacheco, Bull. Soc. Chim. France, No. 6, 2466 (1972).
E. Gareia, J. Amer. Chem. Soc.,82. 4430 (1960).
T. Batkowski, D. Tomasik, and P. Tomasik, Roczn. Chem.,41, 2101 (1967).
I. J. Fergusson, M. R. Grimmett, and K. Schofield, Tetrahedron Lett., No. 27, 2771 (1972).
J. W. Barnett, I. J. Fergusson, and K. Schofield, unpublished data cited by K. Schofield, M. R. Grimmett, and B. R. T. Keene, in: Heteroatomatic Nitrogen Compounds. The Azoles, Cambridge Univ. Press (1976), p. 68.
M. W. Austin, J. R. Blackborow, J. H. Ridd, and B. V. Smith, J. Chem. Soc., No. 2, 1051 (1965).
I. I. Grandberg, S. V. Tabak, N. I. Bobrova, A. N. Kost, and L. G. Vasina, Khim. Geterotsikl. Soedin., No. 3, 407 (1965).
G. Travagli, Gazz. Chim. Ital.,85, 926 (1955).
S. L. Gusinskaya, Khim. Geterotsikl. Soedin., No. 3, 345 (1970).
O. P. Shvaika and G. P. Klimisha, Khim. Geterotsikl. Soedin., No. 1, 19 (1966).
R. Gompper and H. Ruhle, Ann.,626, 83 (1959).
H. S. Suri, G. N. Sharma, and K. S. Narang, J. Indian Chem. Soc.,45, 409 (1968); Chem. Abstr.,69, 77146 (1968).
R. Gompper and O. Christman, Chem. Ber.,92, 1944 (1959).
L. I. Belen'kii and M. A. Cheskis, Khim. Geterotsikl. Soedin., No. 7, 881 (1984).
L. I. Belen'kii, G. P. Gromova, M. A. Cheskis, and Ya. L. Gol'dfarb, Chemica Scripta,25, 295 (1985).
M. A. Khan, B. M. Lynch, and Y.-Y. Hung, Can. J. Chem.,41, 1540 (1963).
B. M. Lynch and Y.-Y. Hung, Can J. Chem.,42, 1605 (1964).
M. R. Grimmett, S. R. Hartshorn, K. Schofield, and J. B. Weston, J. Chem. Soc., Perkin 2, No. 11, 1654 (1972).
S. D. Sokolov and I. M. Yudintseva, Zh. Org. Khim.,7, 1765 (1971).
R. G. Jones and C. Ainsworth, J. Amer. Chem. Soc.,77, 1538 (1955).
R. Hüttel and A. Gebhardt, Ann.,558, 43 (1947).
R. Hüttel and G. Welzel, Ann.593. 207 (1955).
R. Stolle and F. Henke-Stark, J. Prakt. Chem.,124, 261 (1930).
V. P. Karavai and P. N. Gaponik, Khim. Geterotsikl. Soedin., No. 4, 564 (1985).
B. M. Lynch, Can. J. Chem.,41, 2380 (1963).
B. M. Lynch and T. Chan, Can. J. Chem.,41, 274 (1963).
H. El-Khaden, H. A. R. Mansour, and M. H. Meshreki, J. Chem. Soc. (C), No. 11, 1329 (1968).
E. Lippmann and A. Könnecke, Z. Chem.,15, 226 (1975).
H. W. Gschwend and H. R. Rodriguez, Organic Reactions, Vol. 26, Wiley & Sons, New York (1979), p. 1.
R. Hüttel and F. Buehele, Chem. Ber.,88, 1586 (1955).
J. W. A. M. Janssen, H. J. Koeners, C. G. Kruse, and C. L. Habraken, J. Org. Chem.,38, 1777 (1973).
S. S. Novikov, L. I. Khmel'nitskii, O. V. Lebedev, V. V. Sevast'yanova, and L. V. Epishina, Khim. Geterotsikl. Soedin., No. 4, 503 (1970).
R. Miethchen and C.-F. Kroger, Z. Chem.,7, 184 (1967).
C.-F. Kroger and H. Frank, Angew. Chem.,77, 425 (1965).
C.-F. Kroger and H. Frank, Angew. Chem.,77, 928 (1965).
C.-F. Kroger and R. Miethchen, Chem. Ber.,100, 2250 (1967).
J. H. Ridd, J. Chem. Soc., No. 4, 1238 (1955).
A. Grimison and J. H. Ridd, J. Chem. Soc., Nos. 9/10, 3019 (1959).
L. Schutte, P. P. Kluit, and E. Havinga, Tetrahedron, Suppl. No. 7, 295 (1966).
R. Breslow, J. Amer. Chem., Soc.,79, 1762 (1957).
H. A. Staab, H.-Th. Wu, A. Mannschreck, and G. Schwalbach, Tetrahedron Lett., No. 15, 845 (1964).
P. Haake, L. P. Bausher, and W. B. Miller, J. Amer. Chem. Soc.,91, 1113 (1969).
J. D. Vaughan, Z. Mughrabi, and E. C. Wu, J. Org. Chem.,35, 1141 (1970).
R. A. Coburn, J. M. Landesberg, D. S. Kemp, and R. A. Olofson, Tetrahedron,26, 685 (1970).
R. A. Olofson, W. R. Thompson, and J. S. Michelman, J. Amer. Chem. Soc.,86, 1865 (1964).
R. A. Olofson and J. M. Landesberg, J. Amer. Chem. Soc.,88, 4263 (1966).
E. C. Wu and J. D. Vaughan, J. Org. Chem.,35, 1146 (1970).
H. Kohn, S. J. Benkovic, and R. A. Olofson, J. Amer. Chem. Soc.,94, 5759 (1972).
E. Regel and K.-H. Buchel, Ann., No. 1, 145 (1977).
A. Medici, G. Fantin, M. Fogagnolo, P. Pedrini, A. Dondoni, and G. D. Andreetti, J. Org. Chem.,49, 590 (1984).
E. Regel, Ann., No. 1, 159 (1977).
R. Fusco, F. D'Ado, and A. Masserini, Gazz. Chim. Ital.,96, 1084 (1966).
A. Medici, M. Fogagnolo, P. Pedrini, and A. Dondoni, J. Org. Chem.,47, 3844 (1982).
A. Dondoni, G. Fantin, M. Fogagnolo, A. Mastellari, A. Medici, and P. Pedrini, J. Org. Chem.,49, 3478 (1984).
E. Anders, H.-G. Boldt, R. Fuchs, and T. Gassner, Tetrahedron Lett.,25, 1715 (1984).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 749–773, June, 1986.
Rights and permissions
About this article
Cite this article
Belen'kii, L.I. Effect of the acid-base properties of heteroaromatic compounds on their electrophilic substitution reactions (review). Chem Heterocycl Compd 22, 587–608 (1986). https://doi.org/10.1007/BF00575238
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00575238