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Base‐catalyzed redox reactions of α‐hydroxyalkylazaaromatic N ‐oxides
Author(s) -
Muth Chester W.,
Patton Jesse C.,
Bhattacharya Bhabatosh,
Giberson David L.,
Ferguson Christopher A.
Publication year - 1972
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570090621
Subject(s) - chemistry , redox , pyridine , inorganic chemistry , sodium hydroxide , hydrochloric acid , aqueous solution , pyridine n oxide , hydroxide , oxide , medicinal chemistry , organic chemistry
The (α‐hydroxybenzyl)pyridine 1‐oxides on heating with aqueous sodium hydroxide yielded the corresponding benzoylpyridines in redox reactions. When the phenyl groups of the foregoing compounds was replaced by hydrogen or methyl the redox reactions occurred less readily. A kinetic isotope effect of 3 was found for 4‐(α‐deuterio‐α‐hydroxybenzyl)pyridine 1‐oxide on reaction with sodium hydroxide. The removal of the α‐deuterio group is non‐reversible. A mechanism consistent with these observations is given. 6‐Acetoxyphenanthridine 5‐oxide yielded with concentrated hydrochloric acid a redox product, 6‐formylphenanthridine hydrochloride, whereas under the same conditions neither (α‐hydroxybenzyl)pyridine 1‐oxides nor 2‐hydroxy‐methylquinoline 1‐oxide yielded a redox product.