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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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2212–2217, November, 1995.
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Krasnaya, Z.A., Bogdanov, V.S., Burova, S.A. et al. Synthesis of δ-cyclohexyl- and δ,δ-alkylene-α,α-dicarbonyl-substituted dienes and study of their valence isomerization. Russ Chem Bull 44, 2118–2123 (1995). https://doi.org/10.1007/BF00696716
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DOI: https://doi.org/10.1007/BF00696716