75839-82-6Relevant articles and documents
Separation of cis/trans-cyclohexanecarboxylates by enzymatic hydrolysis: Preference for diequatorial isomers
Koenigsberger, Kurt,Luna, Hector,Prasad, Kapa,Repic, Oljan,Blacklock, Thomas J.
, p. 9029 - 9032 (1996)
4-Substituted cis/trans-cyclohexanecarboxylates have been separated into the isomers by enzymatic hydrolysis with lipase from Candida rugosa with very good selectivity. The enzyme preferentially recognizes diequatorial conformations. Copyright (C) 1996 Elsevier Science Ltd.
Electroorganic Reactions. Part 37. The Stereochemistry and Mechanism of the Cathodic Hydrogenation of Methyl 4-tert-Butylcyclohex-1-enecarboxylate
Matteis, Cristina I. De,Utley, James H. P.
, p. 879 - 883 (2007/10/02)
Methyl 4-tert-butylcyclohex-1-enecarboxylate is hydrogenated at a mercury cathode, in the presence of proton donors, in a smooth 2 F mol-1 process.The proportions of cis and trans isomers in the product (methyl 4-tert-butylcyclohexanecarboxylate) are a function of reaction conditions and detailed consideration shows that the reaction is under kinetic control.Protonation of the first-formed radical anion is probably at C-1, with little stereoselectivity.The results of base- and radical-induced epimerizations of 1,4-disubstituted cyclohexanes were used to establishthe likely outcome of thermodynamic control.These results are in impressive agreement with calculations based on substituent group conformational preferences.
