Summary
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1.
Condensations were carried out between the 1-alkyl-1,3-butadienes (piperylene, 5-methyl-1,3-hexadiene, 1,3-octadiene, and 5,5-dimethyl-1,3-hexadiene) and acrylic, methacrylic, and 2-isopropylacrylic esters, and the relative amounts of the structural isomers formed were determined.
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2.
The relative amount of the m-isomer in the mixture of adducts increases with increase in the sizes of the alkyl substituents in the diene and dienophile, which finds its explanation in increased steric hindrance to the formation of the o-isomer.
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3.
In the case of the condensation of piperylene with methyl acrylate it was shown that with rise in temperature the content of m-isomer in the mixture of adducts increases.
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Nazarov, I.N., Titov, Y.A. & Kuznetsova, A.I. Structural orientation in diene condensations of 1-alkyl-1,3-butadienes with unsymmetric dienophiles. Russ Chem Bull 9, 819–825 (1960). https://doi.org/10.1007/BF01179181
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DOI: https://doi.org/10.1007/BF01179181