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Issue 13, 1974
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The conformational analysis of saturated heterocycles. Part LXIV. Stereochemical orientation of the ethylation of piperidines

Abstract

Rates of reaction of a series of 1-alkyl-4-phenylpiperidines with ethyl iodide in methanol and in acetonitrile and the proportions of the isomeric quaternary salts formed are reported. Axial ethylation predominates for all cases studied, but the equatorial:axial product ratios often approach unity, and the stereoselectivity is intermediate between those found for methylation (preference for axial attack) and benzylation (preference for equatorial attack).

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Article information


J. Chem. Soc., Perkin Trans. 2, 1974, 1557-1561
Article type
Paper

The conformational analysis of saturated heterocycles. Part LXIV. Stereochemical orientation of the ethylation of piperidines

V. J. Baker, I. D. Blackburne and A. R. Katritzky, J. Chem. Soc., Perkin Trans. 2, 1974, 1557
DOI: 10.1039/P29740001557

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