Conclusions
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1.
2-Methyl-2-phenyl-1,3-dioxa-5,6-benzocycloheptene and its isomeric 4-methyl-substituted derivatives exist in the twist conformation.
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2.
In the PMR of these compounds the benzyl protons and 4-methyl groups are coupled and the screening influence of the 2-phenyl substituent on the gauche-oriented methylene protons was revealed.
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B. A. Arbuzov, E. N. Klimovitskii, A. B. Remizov, and M. B. Timirbaev, Zh. Obshch. Khim.,51, 2705 (1981).
E. N. Klimovitskii, M. B. Timirbaev, and B. A. Arbuzov, Zh. Obshch. Khim.,54, 2360 (1984).
R. St-Amour and M. St-Jacaues, Can. J. Chem.,59, 2283 (1981).
R. St-Amour and M. St-Jacques, Can. J. Chem.,61 109 (1983)
A. Blanchette, R. Sauriol-Lord, and M. St-Jacques, J. Am. Chem. Soc.,100, 4055 (1978).
J. Soulier, M. Farines, A. Laguerre, and A. Bonafos-Bastouill, Bull. Soc. Chim. France, 307 (1976).
B. A. Arbuzov, E. N. Klimovitskii, A. B. Remizov, and M. B. Timirbaev, Izv. Akad. Nauk SSSR, Ser. Khim., 1030 (1981).
W. F. Bailey and E. L. Eliel, J. Am. Chem. Soc.,96, 1798 (1974).
E. L. Eliel, W. F. Bailey, K. W. Wiberg, H. Connon, and F. W. Nader, Lieb. Ann. Chem., 2240 (1976).
E. N. Klimovitskii, G. N. Sergeeva, K. M. Enikeev, A. V. Il'yasov, and B. A. Arbuzov, Izv. Akad. Nauk SSSR, Ser. Khim., 1309 (1985).
V. N. Petrov, I. A. Litvinov, Yu. T. Struchkov, E. N. Klimovitskii, M. B. Timirbaev, and B. A. Arbuzov, Zh. Obshch. Khim.,53, 132 (1983).
W. J. Orville-Thomas (ed.), Internal Rotation in Molecules, Wiley-Interscience (1974).
Yu. Yu. Samitov, Atlas of PMR Spectra of Stereoisomers [in Russian], Vol. 1, Kazan' University (1978).
F. W. Nader, Tetrahedron Lett., 1591 (1975).
D. L. Rakhmankulov, A. M. Syrkin, E. A. Kantor, and S. S. Zlotskii, Physicochemical Constants of Oxygen-Containing Heterocyclic Compounds [in Russian], Ufimsk Petroleum Institute (1974).
E. N. Klimovitskii, G. N. Sergeeva, D. Yu. Strel'nik, and B. A. Arbuzov, Izv. Akad. Nauk SSSR, Ser. Khim., 2259 (1984).
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Translated from Izvestiya Akademii Nauk SSSR, No. 5, pp. 1072–1076, May, 1986.
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Arbuzov, B.A., Klimovitskii, E.N., Sergeeva, G.N. et al. Stereochemistry of seven-membered heterocycles. Communication 17. PMR spectra and conformation of 2-methyl-2-phenyl-1, 3-dioxa-5,6-benzocycloheptene and its isomeric 4-methyl derivatives. Russ Chem Bull 35, 971–974 (1986). https://doi.org/10.1007/BF00955360
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DOI: https://doi.org/10.1007/BF00955360