Nature 139, 718-719 (24 April 1937) | doi:10.1038/139718b0

Isomerism of Derivatives of Cyclohexane

R. D. DESAI ,  R. F. HUNTER &  G. S. SAHARIA

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BOTH 4-methylcyclohexane-l-carboxy-l-succinic acid and 3-methylcyclohexane-l-carboxy-l-succinic acid, synthesized by condensation of ethyl bromoacetate with the sodio derivatives of the dicyano esters prepared by Higson and Thorpe’s method1, have been isolated in two forms ; there being no indication of isomerism connected with multiplanar forms2. This method provides a satisfactory synthesis of the tricarballylic acids derived from cyclic ketones, and the low yield of -dimethyltricarballylic acid obtained from acetone3 can be raised to nearly 30 per cent by suitable modification of the method. The conversion of the tricarballylic derivatives into the corresponding aconitic acids is being investigated.

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References

  1. Higson and Thorpe, J. Chem. Soc., 89, 1455 (1906).
  2. Desai, Hunter, Ghulam Khan and Saharia, J. Chem. Soc., 416 (1936); Waheed Bukhsh, Desai, Hunter and Mehdi Hussain, J. Chem. Soc., 1159 (1936); Desai, Farooq and Hunter, J. Chem. Soc., 1162 (1936).
  3. Clemoand Welch, J. Chem. Soc., 2621 (1928).