Pyridinium compounds. Part I. Carbon–nitrogen bond cleavage in p-nitrobenzylpyridinium ion and related α-substituted derivatives by aqueous sodium hydroxide
Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690002511
Abstract
Treatment of N-(p-nitrobenzyl)pyridinium benzenesulphonate with aqueous sodium hydroxide gives pp′-di-formylazoxybenzene (40%), C-(p-nitrophenyl)-N-benzaldehyde nitrone (30%) and p-nitrobenzaldehyde (7·5%). N-(1-p-Nitrophenylethyl)pyridinium benzenesulphonate and N-(p-nitrodiphenylmethyl)pyridinium benzenesulphonate react with aqueous sodium hydroxide to give pp′-diacetylazoxybenzene (75%) and p-nitrobenzophenone (40%) respectively. The nature of the substituents on the benzylic carbon affects the nature of the products.
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Journal Name：Journal of the Chemical Society C: Organic
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CAS no.: 89640-58-4
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