The stereochemistry of N-methyl-3-(P-fluoro-benzoyl)-4-hydroxy-4-(P-fluorophenyl)piperidine

Abstract

A rigorous assignment of the stereochemistry of substituted piperidines of the type 1 has not been reported. However, a paper by Unkovskii, et al., reporting infrared spectral studies of intramolecular hydrogen bonding in closely similar systems suggests that the bulky benzoyl and phenyl groups would be most energetically favored disposed in the trans-diequatorial configuration of the piperidine ring (chair form, 2). This evidence is, however, equivocal because such bonding is also possible in other conformations.

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