Synthesis of δ-cyclohexyl- and δ,δ-alkylene-α,α-dicarbonyl-substituted dienes and study of their valence isomerization |
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Authors: | Zh. A. Krasnaya V. S. Bogdanov S. A. Burova Yu. V. Smirnova |
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Affiliation: | 1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation 2. Higher Chemical College of Russian Academy of Sciences, 9 Miusskaya pl., 125190, Moscow, Russian Federation
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Abstract: | β-Cyclohexylacrolein, β-cyclohexylmethacrolein, or α-cycloalkylidenalkanals were condensed with methyl acetoacetate or dimethyl malonate to give the δ-cyclohexyl- and δ,δ-alkylene-substituted α,α-dicarbonyl-containing α,β∶γ,δ-dienes. The structures of the reaction products were studied using1H NMR,13C NMR, and UV spectroscopy. The diene keto esters bearing no substituents at the γ-position were shown to be in fact three-component equilibrium mixtures comprised ofE- andZ-isomers of the diene (at the α,β bond) and a corresponding 2H-pyran. On the other hand, for keto esters with a Me group at the γ-position the equilibrium is shifted entirely to the 2H-pyrans. In contrast with the keto esters, dienic diesters exist only in the open form. |
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