- Experiments on the Chaperon effect in the nitration of aromatics
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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 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 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 were compared with the corresponding classical nitration in H2SO4.
- Strazzolini, Paolo,Giumanini, Angelo G.,Runcio, Antonio,Scuccato, Massimo
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p. 952 - 958
(2007/10/03)
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- A Mild Oxidation of Aromatic Amines
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Several primary aromatic amines have been converted to the corresponding nitro compounds in good yields.The oxidant was oxone (potassium peroxymonosulfate) and the reactions were performed in 5 to 20percent aqueous acetone and buffered with sodium bicarbonate.
- Webb, Kevin S.,Seneviratne, Viran
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p. 2377 - 2378
(2007/10/02)
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- 1-Aryl-3-(2-chloroethyl) ureas: Synthesis and in vitro assay as potential anticancer agents
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1-Aryl-3-(2-chlorethyl) ureas and 1-aryl-3-nitrose-3-(2-chloroethyl) ureas, derived from 4-phenylbutyric acid and alkylanillines, were synthesized and their cytotoxicity was evaluated on human adenocarcinoma cells in vitro. Methyl 4-[p-[3-(2-chloroethyl)ureido]-phenyl]butyrate, 4-methyl [3-(2-chloroethyl)ureido]benzene, and 4-butyl[3-(2-chloroethyl)ureido]benzene were found to be at least as cytotoxic as 4-[p-[bis-(2-chloroethyl)amino]phenyl]butyric acid (chlorambucil), while their N-nitrose derivatives were inactive.
- Gaudreault,lacroix,Page,Joly
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p. 185 - 187
(2007/10/02)
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