New insights into the acid-promoted reaction of caffeic acid and its esters with nitrite: decarboxylation drives chain nitrosation pathways toward novel oxime derivatives …

A Napolitano, M d'Ischia

Index: Napolitano, Alessandra; D'Ischia, Marco Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 803 - 810

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Citation Number: 34

Abstract

In 0.05 M acetate buffer, pH 4, containing 1% methanol, caffeic acid (1a)(2× 10-3 M) reacted smoothly with nitrite (NO2-)(4× 10-3 M) to afford as main products the novel 2-hydroxy-and 2- methoxyaldoximes 7a, b, the 2-oxoaldoxime 9a, 3, 4-dihydroxybenzoic acid, 3, 4- dihydroxybenzaldehyde, and the known furoxan 3c and benzoxazinone 4b in smaller amounts. At lower 1a concentration (eg, 1× 10-4 M), 7a was the main product, whereas ...