Issue 0, 1967

The preferred steric course of quaternisation of 1-alkylpiperidines

Abstract

Previous methods of assignment of configuration to pairs of diastereoisomeric quaternary salts of type [double bond splayed left]+NR1R2X, [double bond splayed left]+NR2R1X derived from N-alkylpiperidines are re-examined and their general utility confirmed. Our previous conclusion, that axial attack is preferred in most reactions of marked stereoselectivity, is extended to cover a preference of boat-axial (formally, equatorial) attack in certain 3-azabicyclo[3,3,1]nonanes. The ambiguous position regarding quaternisations of N-alkylnor-tropanes, -tropines, and -pseudotropines is discussed. Other workers' results, arguments, and conclusions are examined

Article information

Article type
Paper

J. Chem. Soc. B, 1967, 1184-1195

The preferred steric course of quaternisation of 1-alkylpiperidines

D. R. Brown, R. Lygo, J. McKenna, J. M. McKenna and B. G. Hutley, J. Chem. Soc. B, 1967, 1184 DOI: 10.1039/J29670001184

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