Conclusions
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1.
p-Substituted phenyl formates exist in solution in CCl4 at 25‡C in the form of an equilibrium mixture of 90±10% Z conformers and 10±10% E conformers with respect to the esteric group.
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2.
Phenyl formates are characterized in solutions by the rotation of the phenyl ring through ∿65‡ relative to the common plane of the molecule.
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A. A. Bredikhin, L. V. Frolova, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1555 (1989).
A. Van Es and W. Stevens, Rec. Trav. Chim.,24, 1247 (1965).
A. A. Bredikhin, P. P. Chernov, V. V. Klochkov, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1552 (1988).
T. Schaefer and G. H. Penner, Can. J. Chem.,65, 2175 (1987).
T. Schaefer, R. Sebastian and G. H. Penner, Can. J. Chem.,66, No. 8, 1787 (1988).
C. Van Alsenoy, J. M. Scarsdale, and L. Schafer, J. Mol. Struct.,90, 297 (1982); K. B. Wiberg and K. E. Laiding, J. Am. Chem. Soc.,109, 593 (1987).
T. B. Grindley, Tetrahedron Lett.,29, 1757 (1982).
R. F. Curl, J. Chem. Phys.,30, 1529 (1959).
A. A. Bredikhin, V. A. Kirillovich, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 795 (1988).
A. N. Vereshchagin, Polarizability of Molecules [in Russian], Nauka, Moscow (1980).
D. A. Sweigart and D. W. Turner, J. Am. Chem. Soc.,94, 5592 (1972).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1560–1564, July, 1989.
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Bredikhin, A.A., Frolova, L.V. & Vereshchagin, A.N. Polarity, polarizability, and structure of esters. 5. Phenyl formates. Russ Chem Bull 38, 1426–1430 (1989). https://doi.org/10.1007/BF00978432
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DOI: https://doi.org/10.1007/BF00978432