Electro-organic reactions. Part 23. Regioselectivity and the stereochemistry of anodic methoxylation of N-acylpiperidines and N-acylmorpholines
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 807-813
- https://doi.org/10.1039/p29840000807
Abstract
Anodic methoxylation of conformationally biassed N-acylpiperidines has been shown to give axial substitution due to steric constraints imposed by relatively slow rotation of the planar N-acyl groups. These steric constraints also account for the regioselectivity of the reaction and the axial substitution resulting from nucleophilic displacement of the α-methoxy-function in the presence of aluminium chloride. The N-acyl groups adopt anti- and syn-conformations and their relative proportions are consistent with the steric factors invoked to explain the substitution pattern.Keywords
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