Tetrahedron Letters

Reaction of caffeic acid derivatives with acidic nitrite

P Cotelle, H Vezin

Index: Cotelle, Philippe; Vezin, Herve Tetrahedron Letters, 2001 , vol. 42, # 19 p. 3303 - 3305

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Citation Number: 28

Abstract

Caffeic derivatives were reacted with acidic nitrite at controlled pH in order to mimic the gastric juice conditions. At pH 2, whereas caffeic acid reacts exclusively on the side chain, its esters are readily nitrated. Under more acidic conditions (pH 1), caffeic acid methyl ester undergoes a dimerisation into a norlignan derivative.