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Substituent effects in the cyclohexenes 1.13C AND1H NMR spectroscopy of cis-4,5-dimethyl-4-cyclohexene and syn-cis-Δ4-octalin-1,2-dicarboxylic acids and their derivatives

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Conclusions

  1. 1.

    CH3 group effects have been determined in the13C spectra of cis-1,4,5-trimethyl4-cyclohexene-, syn-cis-1-methyl-, and syn-cis-2-methyl-Δ4-octalin-1,2-dicarboxylic acids and their derivatives.

  2. 2.

    In the syn-cis-Δ4-octalin-1,2-dicarboxylic acids, and their esters, and in theγ-oxy acids of this same series, the cyclohexene ring is in predominantly in half-chair conformation with the substituent at the C1 atom in the axial position, and the substituent at the C2 atom in the equatorial position.

  3. 3.

    The cyclohexene ring is in the boat conformation in the anhydrides of the syn-cisΔ4-octalin-1,2-dicarboxylic acids and the corresponding lactones.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 777–783, April, 1979.

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Denisenko, V.A., Novikov, V.L. & Elyakov, G.B. Substituent effects in the cyclohexenes 1.13C AND1H NMR spectroscopy of cis-4,5-dimethyl-4-cyclohexene and syn-cis-Δ4-octalin-1,2-dicarboxylic acids and their derivatives. Russ Chem Bull 28, 721–726 (1979). https://doi.org/10.1007/BF00923568

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Keywords

  • Spectroscopy
  • Ester
  • Anhydride
  • Cyclohexene
  • Lactone