A facile thermal equilibration of cis-(3-methoxy-2-piperidyl)-Z-propanone and some analogous cis-(&substituted 2-piperidyI)-Z-propanones with their trans isomers is reported. The effects on the equilibrium of temperature, solvent, pH, and the size of the 3 substituent were investigated. Chemical and nmr spectral data and conformational free-energy calculations are presented to support the assignment of the trans configuration to the more stable isomer.The title compounds are intermediates in the synthesis of febrifugines.A revised synthesis of the title compounds is reported.
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