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

Draper, M. D. and Petracek, F. J. and Klohs, M. W. and Parker, Richard G. and Roberts, John D. (1970) The stereochemistry of N-methyl-3-(P-fluoro-benzoyl)-4-hydroxy-4-(P-fluorophenyl)piperidine. Tetrahedron Letters, 11 (51). pp. 4481-4484. ISSN 0040-4039.

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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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Additional Information:© 1970 Pergamon Press. Received in USA 24 August 1970; received in UK for publication 5 October 1970. The X-ray and nmr studies which were carried on at the California Institute of Technology were supported by the National Science Foundation. Contribution No. 4066.
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Caltech Gates and Crellin Laboratories of Chemistry4066
Issue or Number:51
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Official Citation:M.D. Draper, F.J. Petracek, M.W. Klohs, Richard G. Parker, John D. Roberts, The stereochemistry of N-methyl-3-(P-fluoro-benzoyl)-4-hydroxy-4-(P-fluorophenyl)piperidine, Tetrahedron Letters, Volume 11, Issue 51, 1970, Pages 4481-4484, ISSN 0040-4039, (
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ID Code:61515
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 22:03
Last Modified:03 Oct 2019 09:08

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