Abstract
Electrolysis of aromatic aldehydes and malononitrile in alcohols in an undivided cell in the presence of a NaBr-NaOAc mediatory system stereoselectively gave bicyclic compounds containing the cyclopropane and pyrroline fragments in 60 to 70% yields. In the bicyclic products, the benzene and pyrroline rings are on different sides of the cyclopropane ring.
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References
L. A. Yanovskaya, V. A. Dombrovskii, and A. Kh. Khusid, Tsiklopropany s funktsional’nymi gruppami. Sintez i primenenie [Functionalized cyclopropanes. Synthesis and Applications], Nauka, Moscow, 1980 (in Russian).
T. Tsuji and S. Nishida, The Chemistry of the Cyclopropyl Group, J. Wiley and Sons, New York, 1987.
W. A. Donaldson, Tetrahedron, 2001, 57, 8589.
Organic Electrochemistry, 4th ed., Ed. H. Lund, Marcel Dekker, Inc., New York, 2000.
G. I. Nikishin, M. N. Elinson, and S. K. Feducovich, Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1919 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 35 (Engl. Transl.)].
M. N. Elinson, T. L. Lizunova, M. O. Dekaprilevich, Yu. T. Struchkov, and G. I. Nikishin, Mendeleev Commun., 1993, 192.
M. N. Elinson, T. L. Lizunova, B. I. Ugrak, M. O. Dekaprilevich, and G. I. Nikishin, Tetrahedron Lett., 1993, 33, 5795.
G. I. Nikishin, M. N. Elinson, T. L. Lizunova, and B. I. Ugrak, Tetrahedron Lett., 1991, 32, 2655.
M. N. Elinson, S. K. Feducovich, A. A. Zakharenkov, S. G. Bushuev, D. V. Pashchenko, and G. I. Nikishin, Mendeleev Commun., 1998, 15.
M. N. Elinson, S. K. Feducovich, S. G. Bushuev, D. V. Pashchenko, and G. I. Nikishin, Izv. Akad. Nauk, Ser. Khim., 1998, 1165 [Russ. Chem. Bull., 1998, 47, 1133 (Engl. Transl.)].
M. N. Elinson, S. K. Feducovich, Z. A. Starikova, O. S. Olessova, A. N. Vereshchagin, and G. I. Nikishin, Tetrahedron Lett., 2000, 41, 4937.
M. N. Elinson, S. K. Feducovich, A. N. Vereshchagin, A. S. Dorofeev, D. E. Dmitriev, and G. I. Nikishin, Izv. Akad. Nauk, Ser. Khim., 2003, 2117 [Russ. Chem. Bull., Int. Ed., 2003, 52, 2235 (Engl. Transl.)].
M. N. Elinson, S. K. Feducovich, T. A. Zaimovskaya, A. N. Vereshchagin, and G. I. Nikishin, Izv. Akad. Nauk, Ser. Khim., 2003, 2122 [Russ. Chem. Bull., Int. Ed., 2003, 52, 2241 (Engl. Transl.)].
G. Boche and H. M. Walbirsky, Cyclopropane Derived Intermediates, J. Wiley and Sons, 1990.
J. P. Kutney, J. Wagner, and G. M. Hewitt, Helv. Chim. Acta, 1994, 77, 1707.
J. Salaun and M. S. Baird, Curr. Med. Chem., 1995, 2, 511.
O. E. Nasakin, A. N. Lishchikov, Yu. S. Kayukov, and V. P. Sheverdov, Khim.-Farm. Zh., 2000, 34, No. 4, 17 [Pharm. Chem. J., 2000, 34, 170 (Engl. Transl.)].
M. N. Elinson, S. K. Feducovich, Z. A. Starikova, A. N. Vereshchagin, and G. I. Nikishin, Tetrahedron, 2004, 60, 11743.
M. N. Elinson, S. K. Feducovich, T. L. Lizunova, and G. I. Nikishin, Tetrahedron, 2000, 56, 3063.
M. N. Elinson, S. K. Feducovich, T. L. Lizunova, and G. I. Nikishin, Elektrokhimiya, 1996, 32, 42 [Russ. J. Electrochem., 1996, 32 (Engl. Transl.)].
P. H. Leake, Chem. Rev., 1956, 56, 27.
H. Hart and Y. C. Kim, J. Org. Chem., 1966, 31, 2784.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 663–667, March, 2005.
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Elinson, M.N., Feducovich, ..K., Zaimovskaya, T.A. et al. Stereoselective electrocatalytic transformations of malononitrile and aromatic aldehydes into (1R,5S,6R)*-4,4-dialkoxy-2-amino-6-aryl-1,5-dicyano-3-azabicyclo[3.1.0]hex-2-enes. Russ Chem Bull 54, 673–677 (2005). https://doi.org/10.1007/s11172-005-0304-6
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DOI: https://doi.org/10.1007/s11172-005-0304-6