Abstract
Data on the reaction of oxiranes and oxetanes with carbonyl compounds are correlated. The effect of the nature of the catalyst and the structure of the starting reagents on the selectivity of the reaction and the kinetics, stereochemistry, and mechanism of the reaction are discussed.
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Literature cited
D. L. Rakhmankulov, R. A. Karakhanov, S. S. Zlot-skii, E. A. Kantor, U. B. Imashev, and A. M. Syrkin, in: Progress in Science and Technology. Technology of Organic Substances. Vol. 5. The Chemistry and Technology of 1,3-Dioxacycloalkanes [in Russian], Planning and Surveying Office of the All-Union Institute of Scientific and Technical Information, Moscow (1979).
A. V. Bogat-skii and N. L. Garkovik, Usp. Khim., 37, 581 (1968).
A. Arandale and L. A. Mikeshka, Usp. Khim., 23, 223 (1954).
I. Apjok, M. Bartok, R. A. Karakhanov, and N. I. Shuikin, Usp. Khim., 38, 72 (1969).
M. S. Malinovskii, Oxides of Olefins and Their Derivatives [in Russian], Goskhimizdat, Moscow (1961).
V. N. Yandovskii, V. S. Karavan, and T. I. Temnikova, Usp. Khim., 39, 571 (1970).
D. L. Rakhmankulov, E. A. Kantor, and R. Kh. Nurieva, Deposited Paper No. 4353-79; Ref. Zh. Khim., 18Zhl79 (1980).
O. Meresz, K. P. Leung, and A. S. Denes, Tetrahedron Lett., No. 27, 2797 (1972).
I. G. Tishchenko, O. N. Bubel', G. Z. Stasevich, and A. F. Abramov, Khim. Geterotsikl. Soedin., No. 7, 907 (1975).
Yu. Yu. Samitov, L. P. Glushko, M. S. Malinovskii, and N. I. Pokhodenko, Khim. Geterotsikl. Soedin., No. 4, 447 (1972).
H. D. Scharf and E. Wolters, Chem. Ber., 111, 639 (1978).
I. Mattay, W. Thünker, and H. D. Scharf, Ann. Chem., No. 6, 1105 (1981).
R. P. Hahzlick and M. Leinwetter, J. Org. Chem., 43, 438 (1978).
Yu. K. Vesnin, S. I. Bagaev, and I. N. Yadrinkina, in: Physical Chemistry [in Russian], Vol. 1, Krasnoyarsk (1974), p. 205.
I. R. Kireev, E. A. Kantor, R. B. Valitov, and D. L. Rakhmankulov, Zh. Org. Khim., 17, 1536 (1981).
N. N. Mamedov, M. A. Mamed'yarov, and B. G. Segedova, Azerbaidzhansk. Khim. Zh., No. 2, 41 (1974).
F. Nerdel, I. Budrus, G. Scherowsky, D. Klamman, and M. Fligge, Ann. Chem., 710, 85 (1967).
I. Cano, I. Font, M. A. Galan, and V. Virfili, Afinidad, 35, 123 (1978).
T. I. Temnikova and V. N. Yandovskii, Zh. Org. Khim., 4, 1006 (1968).
N. Blackett, I. M. Coxon, M. P. Hartshorn, A. I. Lewis, G. R. Little, and G. R. Wright, Tetrahedron, 26, 1311 (1970).
O. N. Bubel', I. G. Tishchenko, G. Z. Stasevich, I. L. Romanko, A. F. Abramov, and E. D. Skakovskii, Khim. Geterotsikl. Soedin., No. 6, 888 (1979).
S. Watanabe, T. Fujita, and K. Suga, Yuki Gosei Kagaku Kyokaishi, 35, 290 (1977); Ref. Zh. Khim., 11Zh225 (1978).
L. P. Glushko, N. I. Pokhodenko, M. S. Malinovskii, and E. G. Sumbaev, Zh. Org. Khim., 7, 1591 (1971).
D. L. Rakhmankulov, E. A. Kantor, R. Kh. Nurieva, P. S. Belov, N. E. Maksimova, and B. M. Brudnik, USSR Inventor's Certificate No. 541845; Byull. Izobret., No. 1 (1977).
A. A. Petrov, Zh. Obshch. Khim., 10, 981 (1940).
V. N. Yandovskii and T. I. Temnikova, Zh. Org. Khim., 4, 1758 (1968).
T. I. Temnikova, B. A. Gontarev, and R. Gissel', Zh. Obshch. Khim., 30, 2457 (1960).
T. I. Temnikova and B. A. Gontarev, Zh. Obshch. Khim., 33, 3799 (1963).
T. I. Temnikova and B. A. Gontarev, Zh. Obshch. Khim., 34, 24 (1964).
G. Willfang, Ber., 74, 145 (1941).
D. L. Rakhmankulov, E. G. Galkin, E. M. Vyrypaev, R. Kh. Nurieva, A. M. Syrkin, and E. A. Kantor, Zh. Prikl. Khim., 51, 1356 (1978).
C. Fauran, I. Eberle, M. Fasäuelle, and P. Burnier, Eur. J. Med. Chem., 9, 281 (1974).
C. Fauran, M. Turin, G. Raynaud, and I. Thomas, French Patent No. 2190435; Chem. Abstr., 84, 31131 (1976).
E. R. Warawa, US Patent No. 4046892; Ref. Zh. Khim., 90116 (1978).
R. G. Shin, V. V. Tatarchuk, and G. F. Skiba, Paper deposited at VINITI, No. 1953-75; Ref. Zh. Khim., 24Zh214 (1975).
Z. B. Éfendiev, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 20, 1578 (1977).
R. M. Ivadova, M. A. Mamedov, M. M. Guseinov, I. M. Akhmedov, and N. Ismailov, in: Epoxide Monomers and Epoxide Resins [in Russian], edited by M. S. Salakhov, Elm, Baku (1975), p. 82.
H. O. House, J. Am. Chem. Soc., 77, 5083 (1955).
W. V. Connell and W. H. Moore, J. Org. Chem., 30, 3480 (1965).
V. C. Dryuk, V. I. Avramenko, and V. N. Yandovskii, J. Chem. Soc., Perkin Trans. II, No. 12, 1526 (1977).
H. Meerwein, Angew. Chem., 67, 374 (1955).
K. Bodenbenner, Ann. Chem., 623, 183 (1959).
W. G. Bailley and R. L. Sun, Polym. Prep. Am. Chem. Soc., Div. Polym. Chem., 13, 281 (1972).
V. S. Étlis, A. B. Bulovyatova, F. N. Shomina, and E. A. Semenova, Zh. Org. Khim., 18, 1830 (1982).
T. Bersin and G. Willfang, Chem. Ber., 70, 2167 (1937).
Y. Fujita, T. Morimoto, and T. Nakano, Japanese Patent No. 7226786; Chem. Abstr., 77, 139451 (1972).
B. A. Trofimov, E. P. Vyalykh, and A. S. Atavin, USSR Inventor's Certificate No. 437737; Byull. Izobret., No. 28, 49 (1974).
M. M. Movsumzade, A. L. Shabanov, and G. Kh. Mamedov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 22, 758 (1979).
G. Kh. Mamedov, M. M. Movsumzade, V. S. Mamedzade, A. L. Shabanov, and N. G. Kerimova, Azerbaidzhansk. Khim. Zh., No. 6, 91 (1976).
I. I. Baldwin, South African Patent No. 7604464; Chem. Abstr., 88, 37802 (1978).
K. Eichenberger, H. Kuehnis, F. Ostermayer, and H. Schroeter, West German Patent No, 2701794; Chem. Abstr., 87, 152208 (1977).
I. Somlo and F. Widmer, West German Patent No. 2548179; Chem. Abstr., 85, 108664 (1976).
Z. Manasek and I. Luiston, Czechoslovakian Patent No. 164143; Ref. Zh. Khim., 3N181P (1978).
B. K. Wasson and C. S. Rooney, US Patent No. 3828076; Ref. Zh. Khim., 110217 (1975).
L. S. Stanishevskii, I. G. Tishchenko, and A. Ya. Guzikov, Zh. Org. Khim., 7, 73 (1971).
I. Kagan and B. E. Firth, J. Org. Chem., 39, 3145 (1974).
I. Kagan, I. T. Przybytek, B. E. Firth, and S. P. Singh, Tetrahedron Lett., No. 50, 5133 (1972).
K. Mariama and A. Osuka, Chem. Lett., No. 1, 77 (1979).
R. I. Mustafaev, G. A. Umudov, S. I. Sadykh-Zade, and G. I. Nikishin, in: Problems in Petrochemistry [in Russian], Vol. 3, Élm, Baku (1971), p. 258.
T. A. Umudov, R. I. Mustafaev, and G. I. Nikishin, in: Epoxide Monomers and Epoxide Resins [in Russian], edited by M. S. Salakhov, Elm, Baku (1975), p. 92.
F. Ya. Kasumov, Sh. K. Kyazimov, and R. A. Sultanov, in: Epoxide Monomers and Epoxide Resins [in Russian], edited by M. S. Salakhov, Elm, Baku (1975), p. 150.
I. N. Siraeva, E. A. Kantor, I. R. Kireev, R. B. Valitov, and D. L. Rakhmankulov, React. Kinet. Catal. Lett., 17, 281 (1981).
G. B. Sergeev, M. M. Movsumzade, S. V. Zenin, A. L. Shabanov, S. I. Akhmedov, V. V. Smirnov, and V. A. Polyakov, Vestn. Mosk. Gos. Univ., Khim., 16, 174 (1975).
R. Kh. Nurieva, I. N. Siraeva, E. A. Kantor, and D. L. Rakhmankulov, React. Kinet. Catal. Lett., 11, 259 (1979).
I. N. Siraeva and E. A. Kantor, in: Current Problems in Petrochemistry [in Russian], Ufa (1979), p. 27.
I. N. Siraeva and E. A. Kantor, in: State of Scientific Research on the Solution of Problems of the Petroleum-Gas Industry by Means of Complex Programs [in Russian], Ufa (1979), p. 153.
D. L. Rakhmankulov, R. Kh. Nurieva, E. A. Kantor, and P. S. Belov, Zh. Prkkl. Khim., 50, 212 (1977).
I. G. Tishchenko, O. N. Bubel', and G. Z. Stasevich, Khim. Geterotsikl. Soedin., No. 7, 885 (1974).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3., pp. 291–306, March, 1984.
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Rakhmankulov, D.L., Chalova, O.B., Kiladze, T.K. et al. Reaction of oxiranes and oxetanes with carbonyl compounds. Synthesis of 1,3-dioxacycloalkanes (review). Chem Heterocycl Compd 20, 231–244 (1984). https://doi.org/10.1007/BF00515627
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DOI: https://doi.org/10.1007/BF00515627