Conclusions
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1.
The carbonyl group of benzoylcyclopropanes containing a chlorinated three-membered ring is rotated out of the bisector plane by an angle of 30–40°; in the presence of cis substitutents the direction of this rotation is such as to increase the distance between these substituents and the carbonyl hydrogen.
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2.
The phenyl radicals are rotated by an angle of 15–40° with respect to the carbonyl plane, the direction of rotation being such as to increase the distance between the most closely neighboring hydrogen atoms.
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Literature cited
A. N. Vereshchagin, S. G. Vul'fson, A. I. Donskova, and V. I. Savin, Dokl. Akad. Nauk SSSR,215, 339 (1974).
S. G. Vul'fson, A. I. Donskova, A. N. Vereshchagin, and V. I. Savin, Izv. Akad. Nauk SSSR, Ser. Khim., 76 (1975).
B. A. Arbuzov, A. I. Donskova, S. G. Vul'fson, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim., 1498 (1975).
A. H. Cowley and T. O. Furth, J. Am. Chem. Soc.,91, 39 (1969).
L. S. Bartell, R. L. Carrol, and J. P. Gullory, Tetrahedron Lett., 705 (1964).
L. S. Bartell and J. P. Gullory, J. Chem. Phys.,43, 647 (1965).
J. P. Pierre and P. Arnoud., Bull. Soc. Chim. France, 1690 (1966).
M. J. Aroney, K. E. Calderbank, and H. J. Stootman, J. Chem. Soc. Perkin Trans.,2 (1973), 1365.
A. de Meijere and W. Luttke, Tetrahedron Lett., 2047 (1969).
L. S. Bartell, J. P. Gullory, and A. T. Parks, J. Phys. Chem.,69, 3043 (1965).
M. T. Rogers and J. D. Roberts, J. Am. Chem. Soc.,68, 843 (1946).
W. H. Flygare, A. Narath, and W. D. Cwinn, J. Chem. Phys.,36, 200 (1962).
A. N. Vereshchagin and S. G. Vul'fson, Teor. Eksp. Khim.,4, 548 (1968).
C.-Y. Chen and R. J. W., LeFevre, J. Chem. Soc., B, 40 (1966).
O. Exner and V. Jehlička, Collect. Czech. Chem. Commun.,30, 639 (1965).
L. A. Yanovskaya, V. A. Dombrovskii, G. V. Kryshtal', L. G. Vorontsova, M. O. Dekarpilevich, and I. P. Yakovlev, Application of Conformational Analysis to the Synthesis of New Organic Compounds [in Russian], Izd. Odessk. Univ. (1975), p. 167.
M. J. Aroney, M. G. Corfield, and R. J. W. LeFevre, J. Chem. Soc.,1964, 648.
P. H. Gore, P. A. Hopkins, R. J. W. LeFevre, L. Random, and G. L. Ritchie, J. Chem. Soc., B, 120 (1971).
I. G. Tishchenko, O. G. Kulinkovich, and Yu. V. Glazkov, Zh. Org. Khim.,11, 581 (1975).
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A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Branch of the Academy of Sciences of the USSR. Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2239–2243, October, 1976.
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Arbuzov, B.A., Donskova, A.I., Vul'fson, S.G. et al. Kerr constants and spatial structures of chloro-substituted benzocyclopropanes. Russ Chem Bull 25, 2089–2092 (1976). https://doi.org/10.1007/BF02659522
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DOI: https://doi.org/10.1007/BF02659522