Summary
It was shown for the first time that the diene condensation of 2,4-dimethyl-1,3-pentadiene with acrylonitrile results in the formation not only of the ortho isomer (III), but also of the meta isomer (IV) in 3–5% yield.
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I. N. Nazarov, A. I. Kuznetsova, N. V. Kuznetsov, and Yu. A. Titov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (1958), 663.
I. N. Nazarov, A. I. Kuznetsova, and N. V. Kuznetsov, J. Gen. Chem. 25, 88 (1955).
O. N. Jitkow and M. T. Bogert, J. Am. Chem. Soc. 63, 1979 (1941).
M. Neaf and Cie, French Patent 672,025; Chem. Zbl. 1, 2796 (1930).
U. Steiner and H. Schinz, Helv. chim. acta 34, 1176 (1951).
Swiss Patent 143,242-143,257; Chem. Zbl. 1, 2938 (1931).
O. Diels and K. Alder, Leibigs Ann. Chem. 470, 62 (1929).
J. C. Lunt and F. Sondheimer, J. Chem. Soc. (1950), 2957.
O. Diels and K. Alder, German Patent 526,168; Frdl. 17, 410 (1930).
J. C. Lunt and F. Sondheimer, J. Chem. Soc. (1950), 3361.
K. Alder and W. Vogt, Liebigs Ann. Chem. 564, 120 (1949).
R. Ya. Levina, N. N. Godovikov, and F. K. Velichko, J. Gen. Chem. 25, 2522 (1955).
H. Pines, E. F. Jenkins, and V. N. Ipatieff, J. Am. Chem. Soc. 75, 6226 (1953).
J. P. Ferrin et al., J. Organ. Chem. 19, 923 (1954).
I. N. Nazarov, N. V. Kuznetsov, and A. V. Semenovskii, Proc. Acad. Sci. USSR 99, 1003 (1954).
R. Ya. Levina, A. A. Fainzil'berg. and N. P. Shusherina, J. Gen. Chem. 18, 1775 (1948).
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Nazarov, I.N., Mavrov, M.V. Structural orientation in the condensations of 2.4-dimethyl-1,3-pentadiene. Russ Chem Bull 8, 1031–1033 (1959). https://doi.org/10.1007/BF00916671
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DOI: https://doi.org/10.1007/BF00916671