Abstract
Various methods for the preparation of 2,3-dihydrofuran, 2,5-dihydrofuran, 2-methylenetetrahydrofuran, and their alkyl and aryl derivatives are examined. The most promising method for the preparation of 2,3-dihydrofuran is the conversion of 1,4-butanediol on cobalt catalysts. 2,5-Dihydrofuran is obtained by dehydration of 2-butene-1,4-diol on Al2O3, cobalt-containing and other catalysts, while 2-methylenetetrahydrofuran is obtained by dehydrohalogenation of tetrahydrofurfuryl halides. The various methods for the isomerization of 2,5-dihydrofuran to 2,3-dihydrofuran are discussed. Examples of the application of dihydrofurans in organic synthesis are presented.
Similar content being viewed by others
Literature cited
W. J. McKillip and E. Sherman, in: Kirk-Othmer Encyclopedia of Chemical Technology, 3rd edition, Vol. 2, M. Grayson and D. Eckroth, eds., Wiley, New York (1980), p. 499.
R. A. Zhuk, in: Advances in the Chemistry of Furan [in Russian], Zinatne, Riga (1978), p. 184.
D. G. Jones and A. M. Taylor, Q. Rev., 2, 195 (1950).
R. A. Karakhanov, B. B. Blinov, and V. A. Zefirov, USSR Inventor's Certificate No. 46281, Byull. Izobret. No. 43, 57 (1974).
A. A. Ponomarev, in: Syntheses and Reactions of Furan Substances [in Russian], Izd. Saratovsk. Univ., Saratov (1960), p. 85.
I. F. Bel'skii and. N. I. Shuikin, Usp. Khim., 32, 707 (1963).
N. I. Shuikin and I. F. Bel'skii (Belskii), in: Actes Congr. Intern. Catalyse, Paris, No. 2, 2625 (1960).
P. A. Moshkin, D. E. Nosovskii, and D. I. Orochko, Khim. Promst., No. 3, 35 (1967).
A. de Cat, Industrie Chim. Belge, 17, 652, 772, 838, and 1027 (1952); Chem. Abstr., 48, 540 (1958).
D. V. Sokol'skii, M. S. Erzhanova, T. Beisekov, E. Elemesov, and A. Idirisov, Khim. Promst., No. 12, 901 (1978).
N. I. Shuikin, I. F. Bel'skii, and R. A. Karakhanov, Dokl. Akad. Nauk SSSR, 122, 625 (1958).
L. F. Bulenkova, V. M. Gryaznov, Ya. F. Oshis, L. F. Pavlova, and M. V. Shimanskaya, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 696 (1975).
N. I. Shuikin, I. F. Bel'skii, and R. A. Karakhanov, Dokl. Akad. Nauk SSSR, 138, 1136 (1961).
K. S. Topchiev, Dokl. Akad. Nauk SSSR, 19, 497 (1938).
L. Schiepp, H. Geller, and R. Korff, J. Am. Chem. Soc., 69, 672 (1947).
K. Alexander, L. Häfner, G. Smith, and L. Schniepp, J. Am. Chem. Soc., 72, 5506 (1950).
R. A. Karakhanov and B. B. Blinov, Khim. Geterotsikl. Soedin., No. 10, 1434 (1973).
G. P. Nowack and M. M. Johnson, US Patent No. 3828077; Chem. Abstr., 82, 43165 (1975).
L. Pechy, A. Redey, J. Jestzl, G. Gardos, E. Csaszar, and B. Szigeti, Hungarian Patent No. 14927; Chem. Abstr., 89, 163387 (1978).
M. V. Shimanskaya, V. V. Stonkus, Zh. G. Baikova, L. F. Bulenkova, A. Ya. Karmil'chik, A. K. Veinberg, and G. M. Grinherg, USSR Inventor's Certificate No. 671253; Byull. Izobret., No. 14, 274 (1980).
J. W. Kang and W. L. Hergenrother, West German Patent No. 2649900; Chem. Abstr., 87, 135015 (1977).
T. Onota and A. Ono, Japanese Patent No. 54-25017; Ref. Zh. Khim., 12N144P (1980).
V. A. Slavinskaya, D. R. Kreile, É. E. Dzilyuma, and D. É. Sile, Khim. Geterotsikl. Soedin., No. 7, 881 (1977).
J. W. Kang and W. L. Hergenrother, US Patent No. 4129579; Chem. Abstr., 90, 137665 (1979).
C. L. Wilson and W. H. Bagrall, British Patent No. 576553; Chem. Abstr., 42, 2284 (1948).
General Electric Co., Dutch Patent Application No. 7416316; Chem. Abstr., 86, 139823 (1977).
W. E. Smith, US Patent No. 4136099; Ref. Zh. Khim., 17N164P (1979).
V. K. Kamlev, I. K. Sanin, and I. V. Kamenskii, USSR Inventor's Certificate No. 170942; Byull. Izobret., No. 10, 23 (1965)
N. I. Shuikin, M. Bartok, R. A. Karakhanov, and V. M. Shostakovskii, Acta Univ. Szeged, Acta Phys. Chem., 9, 124 (1963).
N. I. Shuikin, I. F. Bel'skii, R. A. Karakhanov, and V. M. Shostakovskii, USSR Inventor's Certificate No. 156559; Byull. Izobret., No. 16, 18 (1963).
A. S. Sultanov, A. K. Khasanov, Z. T. Tukhtamuradov, P. Nasirov, and A. Madzhidov, USSR Inventor's Certificate No. 427729; Byull. Izobret., No. 18, 16 (1974).
I. G. Farbenindustrie A.-G., British Patent No. 510949; Chem. Abstr., 34, 5466 (1940).
P. Dimroth and H. Pasedach, British Patent No. 849192; Chem. Abstr., 56, 456 (1962).
P. Dimroth and H. Pasedach, Angew. Chem., 72, 865 (1960).
I. I. Geiman, L. F. Bulenkova, V. A. Slavinskaya, A. K. Veinberg, A. A. Lazdin'sh, and A. A. Avots, Summaries of Papers Presented at the 3rd All-Union Symposium on Heterogeneous Catalysis in the Chemistry of Heterocyclic Compounds [in Russian], Zinatne, Riga (1981), p. 36.
I. I. Geiman, L. F. Bulenkova, A. A. Lazdin'sh, A. K. Veinberg, V. A. Slavinskaya, and A. A. Avots, Khim. Geterotsikl. Soedin., No. 4, 448 (1981).
R. von Schollner, H. Sugel, and G. Wendt, Z. Anorg. Chem., 432, 231 (1977).
E. E. Mikhlina, A. D. Yanina, and L. N. Yakhontov, Khim.-farm. Zh., No. 6, 26 (1970).
N. Kh. Shtivel', V. E. Nevaeva, and V. S. Markevish, Khim.-farm. Zh., No. 11, 116 (1979).
J. Colonge and R. Gelin, Bull. Soc. Chim. Fr., No. 6, 799 (1954).
N. L. Hause, US Patent No. 275118; Chem. Abstr., 51, 2870 (1957).
N. I. Shuikin, R. A. Karakhanov, I. Ibragimov, and N. L. Komissarova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 122 (1966).
T. E. Londergan, N. L. Hause, and W. R. Schmitz, J. Am. Chem. Soc., 75, 4456 (1953).
V. S. Asmolov, G. Kh. Yamilova, V. M. Shostakovskii, R. A. Karakhanov, and O. M. Nefedov, USSR Inventor's Certificate No. 584006; Byull. Izobret., No. 46, 55 (1977).
O. M. Nefedov, I. E. Dolgii, V. M. Shostakovskii, and M. F. Sisin, USSR Inventor's Certificate No. 663694; Byull. Izobret., No. 19, 80 (1979).
A. P. Terent'ev, M. A. Volodina, N. L. Podlesova, and N. E. Golubeva, Dokl. Akad. Nauk SSSR, 114, 1036 (1957).
D. K. Yur'ev and N. V. Makarov, Zh. Obshch. Khim., 28, 885 (1958).
O. M. Nefedov, V. M. Shostakovskii, I. E. Dolgii, I. K. Anikeev, V. N. Pavlichev, and Yu. M. Luchko, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 234 (1978).
M. Bartok and A. Molnar, Acta Chim. Acad. Hung., 100, 203 (1979).
M. A. Gianturco, P. Friedel, and V. Flanagan, Tetrahedron Lett., No. 23, 1847 (1965).
G. Eglinton, E. R. H. Jones, and M. C. Whriting, J. Chem. Soc., No. 7, 2873 (1952).
L. Crombie, M. Manzoor-i-Kuda, and R. J. D. Smith, J. Chem. Soc., No. 1, 479 (1957).
H. Normant, Chim. Ind., 63, 511 (1950).
L. Crombie, J. Gold, S. H. Harper, and B. J. Stokes, J. Chem. Soc., No. 1, 136 (1956).
R. Paul and S. Tchelitchef, Bull. Soc. Chim. Fr., No. 4, 417 (1953).
C. Botteghi, Gazz. Chim. Ital., 105, 233 (1975).
M. Hajek, P. Silhavy, and J. Malek, Coll. Czech. Chem. Commun., 44, 2393 (1979).
M. G. Vinogradov, N. L. Radyukina, M. S. Pogosyan, S. P. Verenchikov, A. Ya. Shteinshneider, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1949 (1980).
O. E. Nasakin, V. V. Alekseev, and M. P. Vorob'eva, Twelfth Mendeleev Congress on General and Applied Chemistry. Abstracts of the Papers and Communications [in Russian], Vol. 2, Nauka, Moscow (1981), p. 52.
D. M. Aten Armitage and C. L. Wilson, J. Am. Chem. Soc., 81, 2437 (1959).
J. Marc, Compt. Rend., 239, 290 (1954).
W. Reppe, Lieb. Ann., 596, 80 (1955).
N. O. Brace, J. Amer. Chem. Soc., 77, 4157 (1955).
H. B. Singh, G. E. Klinzing, and J. Coull, Ind. Eng. Chem., Prod, Res. Dev., 12, 184 (1973).
Yu. K. Yur'ev, I. K. Korobitsyna, R. D. Benyakir, L. A. Savina, and P. A. Akishin, Vestnik Moskovsk. Gos. Univ., 6, No. 2, 37 (1951).
M. Strohmeyer, West German Patent No. 1211219; Ref. Zh. Khim., 20N115P (1967).
Yu. K. Yur'ev, I. K. Korobitsyna, and E. Kh. Brige, Zh. Obshch. Khim., 20, 744 (1950).
J. Egyed, P. Demerseman, and R. Royer, Bull. Soc. Chim. Fr., No. 11, Part 2, 3014 (1973).
T. N. Shatkina, in: Methods for the Production and Measurement of Radioactive Preparations [in Russian], Atomizdat, Moscow (1960), p. 159.
A. J. Besozzi, S. D. Cooley, and F. E. Potts, US Patent No. 3812158; Ref. Zh. Khim., 5N164P (1975).
R. Romanent, Compt. Rend., 236, 1044 (1953).
F. E. Condon and E. E. Burgoyne, US Patent No. 2650236; Chem. Abstr., 49, 1815 (1955).
I. Ono, T. Yanagihara, H. Okada, T. Kogu, H. Kisaki, and S. Mabuchi, West German Patent No, 2062950; Chem. Abstr., 75, 63592 (1971).
R. G. Wall and V. P. Kurkov, US Patent No. 3996248; Chem. Abstr., 86, 89592 (1977).
V. P. Kurkov, US Patent No. 3932468; Chem. Abstr., 84, 150488 (1976).
A. N. Bashkirov, E. I. Bogolepova, and R. A. Fridman, USSR Inventor's Certificate No. 639883; Byull. Izobret., No. 48, 89 (1978).
E. I. Bogolepova, R. A. Fridman, and A. N. Bashkirov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2429 (1978).
R. Gelin, S. Gelin, and M. Albrand, Bull. Soc. Chim. Fr., No. 2, 720 (1972).
I. F. Bel'skii, N. I. Shuikin, and R. A. Karakhanov, Dokl. Akad. Nauk SSSR, 132, 585 (1960).
R. Bermes, A. Dahmen, H. Hamberger, R. Huisgen, P. De March, and V. Markowski, Collection of Lectures from the 3rd International Symposium on Furan Chemistry (1979), p. 20.
H. Normant, Bull. Soc. Chim. Fr., C, Nos. 3–4, 115 (1951).
J. C. Anderson, D. G. Lindsay, and C. B. Reese, Tetrahedron, 20, 2091 (1964).
W. Rebafka, West German Patent No. 2803987; Chem. Abstr., 91, 179 (1979).
A. J. Hubert, A. Georis, R. Warin, and P. Teyssie, J. Chem. Soc., Perkin Trans. II, No. 4, 366 (1972).
T. Sato, K. Kawashima, O. Maryuama, H. Suehiro, and M. Yokoyama, Japanese Patent Application No. 79-14964; Ref. Zh, Khim., 2N193P (1980).
D. Sh. Ioramashvili, N. P. Karzhavina, and R. A. Karakhanov, Khim. Geterotsikl. Soedin., No. 6, 851 (1980).
P. R. Stapp, G. P. Nowack, and M. M. Johnson, US Patent No. 3651092; Chem. Abstr., 77, 48249 (1972).
W. Hofmann and H. Pasedach, West German Patent No. 1248669; Chem. Abstr., 68, 29574 (1968).
N. I. Shuikin, I. F. Bel'skii (Belskii), and R. A. Karakhanov, Zeitschr. Chem., 3, 222 (1963).
J. Wiemann, M.-R. Monot, and M. L. Bouguerra, Compt. Rend., 259, 2862 (1964).
J. D. Butter and R. D. Laundon, J. Chem. Soc., C, No. 2, 173 (1969).
L. R. Levis, F. H. Schneider, and R. K. Robins, J. Org. Chem., 26, 3842 (1961).
M. J. Rodins, J. R. McCarthy, and R. K. Robins, Biochemistry, 5, 224 (1966).
W. A. Browles, F. H. Schneider, L. R. Levis, and R. K. Robins, J. Med. Chem., 6, 471 (1963).
S. A. Giller, R. A. Zhuk, and M. Yu. Lidak, Dokl. Akad. Nauk SSSR, 176, 332 (1967).
S. A. Giller, R. A. Zhuk, M. Yu. Lidak, and A. A. Zidermane, British Patent No. 1168391; Chem. Abstr., 72, 43715 (1970).
N. A. Chkanikov, G. A. Belitskii, A. Yu. Kolyada, M. G. Kiseleva, I. A. Khitrovo, and M. N. Preobrazhenskaya, Bioorg. Khim., 6, 1316 (1980).
I. I. Grandberg and T. P. Moskvina, Khim. Geterotsikl. Soedin., No. 10, 1366 (1972).
W. Boell, Lieb. Ann., No. 11, 1665 (1979).
van der Bosch, D. K. Steven Ketlenes, and K. B. de Roos, Canadian Patent No. 1051441;
H. Neunhoeffer and H. J. Degen, Chem. Ber., 108, 3509 (1975).
T. Iwashita, T. Kusumi, and H. Kakisawa, Chem. Lett., No. 11, 1337 (1979).
J. Snogl, M. Janda, F. Liska, and J. Slibor, Collect. Czech. Chem. Commun., 45, 888 (1980).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1299–1311, October, 1982.
Rights and permissions
About this article
Cite this article
Slavinskaya, V.A., Karakhanov, R.A., Brezhnev, L.Y. et al. Catalytic synthesis of dihydrofurans (review). Chem Heterocycl Compd 18, 997–1008 (1982). https://doi.org/10.1007/BF00503178
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00503178