Abstract
Under conditions of the phase transfer catalysis, acylation of (thio)phosphorylacetonitriles by (het)aroyl chlorides affords the Z-enol forms of C-acylation products in high yields. Their configurations were studied by IR spectroscopy, dipole moment measurements, and ab initio quantum-chemical calculations [B3LYP/6-31G(d)]. The C=C double bond and the phosphoryl or thiophosphoryl group have an s-cis arrangement. The possibility of strong intramolecular hydrogen bonding in these conformers is the governing factor responsible for the three-dimensional structures of the compounds under investigation. Derivatives of nicotinic acid existing in the individual form as zwitterions are the only exceptions.
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I. L. Odinets, O. I. Artyushin, R. M. Kalyanova, M. Yu. Antipin, K. A. Lysenko, Yu. T. Struchkov, P. V. Petrovskii, T. A. Mastryukova, and M. I. Kabachnik, Zh. Obshch. Khim., 1994, 64, 1957 [Russ. J. Gen. Chem., 1994, 64 (Engl. Transl.)].
I. L. Odinets, O. I. Artyushin, P. V. Petrovskii, K. A. Lysenko, M. Yu. Antipin, Yu. T. Struchkov, T. A. Mastryukova, and M. I. Kabachnik, Zh. Obshch. Khim., 1996, 66, 44 [Russ. J. Gen. Chem., 1996, 66 (Engl. Transl.)].
T. A. Mastryukova, I. L. Odinets, O. I. Artyushin, R. M. Kalyanova, and P. V. Petrovskii, Izv. Akad. Nauk, Ser. Khim., 1998, 1687 [Russ. Chem. Bull., 1998, 47, 1637 (Engl. Transl.)].
T. A. Mastryukova, I. L. Odinets, O. I. Artyushin, R. M. Kalyanova, ?. G. Matveeva, and P. V. Petrovskii, Phosphorus, Sulfur, Silicon and the Related Elements, 1996, 109-110, 577.
E. A. Ishmaeva, Usp. Khim., 1978, 47, 1678 [Russ. Chem. Rev., 1978, 47 (Engl. Transl.)].
E. A. Ishmaeva, Konformatsionnyi analiz elementoorganicheskikh soedinenii [Conformational Analysis of Organometallic Compounds], Nauka, Moscow, 1983, p. 86 (in Russian).
G. C. Pimentel and A. L. McClellan, The Hydrogen Bond, San Francisco-London, Freeman, New York, Reinhold, 1960, 475 pp.
E. A. Ishmaeva, A. N. Vereshchagin, N. A. Bondarenko, G. E. Yastrebova, and A. N. Pudovik, Izv. Akad. Nauk SSSR, Ser. Khim., 1970, 2695 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1970, 29 (Engl. Transl.)].
M. J. Aroney, L. H. Chia, R. J. W. Le Fevre, and J. D. Saxby, J. Chem. Soc., 1964, 2948.
H. J. Geise, Recl. Trav. Chim., 1967, 86, 362.
T. A. Steits and W. N. Lipscomb, J. Am. Chem. Soc., 1965, 87, 2488.
E. A. Ishmaeva, A. P. Timosheva, N. V. Timosheva, and Ya. A. Vereshchagina, Spravochnik po dipol´nym momentam fosfororganicheskikh soedinenii [Handbook of Dipole Moments of Organophosphorus Compounds], Kazan, Izd-vo Kazanskogo Universiteta, 1998, 120 pp. (in Russian).
E. A. Ishmaeva, M. G. Zimin, R. M. Galeeva, and A. N. Pudovik, Izv. Akad. Nauk SSSR, Ser. Khim., 1972, 538 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1972, 31 (Engl. Transl.)].
E. A. Ishmaeva, R. D. Gareev, G. E. Yastrebova, and A. N. Pudovik, Zh. Obshch. Khim., 1972, 42, 73 [J. Gen. Chem. USSR, 1972, 42 (Engl. Transl.)].
O. A. Osipov, V. I. Minkin, and A. D. Garnovskii, Spravochnik po dipol´nym momentam [Handbook of Dipole Moments], Vysshaya Shkola, Moscow, 1971, 414 pp. (in Russian).
Z. Yu. Kokoshko, V. G. Kitaeva, Z. V. Pushkareva, and V. E. Blokhin, Zh. Obshch. Khim., 1967, 37, 58 [J. Gen. Chem. USSR, 1967, 37 (Engl. Transl.)].
E. A. Ishmaeva, O. A. Raevskii, R. A. Cherkasov, F. G. Khalitov, V. V. Ovchinnikov, and A. N. Pudovik, Dokl. Akad. Nauk SSSR, 1971, 197, 862 [Dokl. Chem., 1971 (Engl. Transl.)].
E. A. Ishmaeva, I. I. Patsanovskii, V. Stets, B. Uznanskii, and A. N. Pudovik, Dokl. Akad. Nauk SSSR, 1978, 240, 1361 [Dokl. Chem., 1978 (Engl. Transl.)].
A. N. Vereshchagin and L. A. Grozina, Teor. Eksp. Khim., 1968, 4, 361 [Theor. Exp. Chem., 1968, 4 (Engl. Transl.)].
V. I. Minkin, O. A. Osipov, and Yu. A. Zhdanov, Dipol´nye momenty v organicheskoi khimii [Dipole Moments in Organic Chemistry], Khimiya, Leningrad, 1968, 248 pp. (in Russian).
J. B. Foresman, T. A. Keoth, K. B. Wiberg, J. Snoonian, and M. J. Frisch, J. Phys. Chem., 1996, 100, 16098.
Z. A. Starikova, A. G. Matveeva, and M. P. Pasechnik, Zh. Neorg. Khim., 2002, 47, 1262 [Russ. J. Inorg. Chem., 2002, 47 (Engl. Transl.)].
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Odinets, I.L., Vereshchagina, Y.A., Artyushin, O.I. et al. 3-Aryl(hetaryl)-3-hydroxy-2-phosphorus-substituted acrylonitriles. Synthesis and experimental and theoretical conformational analysis. Russian Chemical Bulletin 52, 638–646 (2003). https://doi.org/10.1023/A:1023906822755
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DOI: https://doi.org/10.1023/A:1023906822755