Conclusions
N-Allylphthalimide oxide and thiooxide exist predominantly in the gauche conformation based on the C-Cring bond, with a syn orientation of the phthalimide group and heteroatom of the three-membered ring. The phthalimide radical protrudes from the plane of N-C-Cring by an angle of 60°.
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Literature cited
R. J. W. Le Fevre, Adv. Phys. Org. Chem.,3, 1 (1965).
A. N. Vereshchagin and O. N. Nuretdinova, Izv. Akad. Nauk SSSR, Ser. Khim.,1970, 1715.
B. A. Arbuzov, A. M. Kamalyutdinova, S. G. Vul'fson, A. N. Vereshchagin, S. M. Shostakovskii, T. K. Voropaeva, and A. A. Retinskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1978, 603.
B. A. Arbuzov, L. A. Grozina, and A. N. Vereshchagin, Teor. Eksp. Khim.,4, 367 (1968).
A. N. Vereshchagin, A. P. Anastas'eva, and S. G. Vul'fson, Izv. Akad. Nauk SSSR, Ser. Khim.,1969, 559.
B. A. Arbuzov, L. K. Novikova, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim.,1978, 1908.
R. P. Bell and J. E. Coop, Trans. Faraday Soc,34, 1209 (1938).
H. Kofod, L. E. Sutton, and J. J. Jackson, J. Chem. Soc.,1952, 1467.
E. G. Cowley and J. R. Partington, J. Chem. Soc.,1933, 1259.
B. A. Arbuzov, L. K. Novikova-Aleksandrova, S. G. Vul'fson, and A. N. Vereshchagin, Izv. Akad. Nauk SSSR, Ser. Khim.,1978, 1932.
D. H. Ball, Y. M. Williams, and L. Long, J. Org. Chem.,28, 1589 (1963).
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Translated from Investiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 664–667, March, 1979.
The authors thank A. M. Salikhov for taking the IR spectra of the studied compounds.
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Arbuzov, B.A., Aleksandrova, L.K., Mullin, V.A. et al. Steric structure of N-allylphthalimide oxide and thiooxide. Russ Chem Bull 28, 618–621 (1979). https://doi.org/10.1007/BF00924853
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DOI: https://doi.org/10.1007/BF00924853