Experiments on the Chaperon effect in the nitration of aromatics

P Strazzolini, AG Giumanini, A Runcio…

Index: Strazzolini, Paolo; Giumanini, Angelo G.; Runcio, Antonio; Scuccato, Massimo Journal of Organic Chemistry, 1998 , vol. 63, # 4 p. 952 - 958

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Citation Number: 39

Abstract

A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in α-position and a dilute solution of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced ortho orientation effect, whereas the hydroxyl group was too prone to ...