A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in alpha-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 or tho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results mere compared with the corresponding classical nitration in H2SO4.
Experiments on the chaperon effect in the nitration of aromatics
STRAZZOLINI, Paolo;GIUMANINI, Angelo;
1998-01-01
Abstract
A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in alpha-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 or tho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results mere compared with the corresponding classical nitration in H2SO4.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
