Nitrogen and Other Heteroatom Nucleophiles

Another approach for oxidative nucleophilic substinition of hydrogen primary amines and CAK m aqueous MeCN fEq 9 45  

Interesting direct a in- dinitrobenzene with primary aj yields of the product fEq. 9.46.  

Ajninadonof 1 100 years. However, this trobenzene and bicyclic appeared for 

1 -Trimethylhyctdzinium iodide is a novel, highly reactive reagent for at via VNS, as shown in Eq 9 49, in which the regioselecdviry is different from that obtained v/ith other reagents 

Seko and coworkers have discovered a convenient copper-catalyzed direct IS v/ith O-alkylhydtoxylamines fEq 9 50  

Amination of heterocyclic nitro compounds such as nitroquinolines, nitroisoquinolines, or nitropyridines can be carried out by means of a liquid ammonia-KMn04 system, which has been studied by Wozniak and coworkers (Eq. 9.44). Frontier molecular orbital calculation can predict the reactivity and regioselectivity of this amination.75 In a similar way, nitroquinolines are methylaminated with a liquid methylamine solution of KMn04.76 

Another approach for oxidative nucleophilic substitution of hydrogen can be carried out with primary amines and CAN in aqueous MeCN (Eq. 9.45).77 

Interesting direct animation of nitroarenes has been reported aromatic photo substitution of m-dinitrobenzene with primary amines is promoted by the presence of fluoride ion to give useful yields of the product (Eq. 9.46).78 

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