Studies on some selective and competitive ...
|Title||Studies on some selective and competitive substitution reactions of cyclopentadienyliron complexed chloronitrobenzenes with amines as nucleophiles.|
|Author(s)||A. Abd-el-Aziz, A. Piorko, C. Lee, R. Sutherland|
|Journal||Section Title: Organometallic and Organometalloidal Compounds, Canadian Journal of Chemistry|
|Abstract||Nucleophilic substitution reactions of the (Î·6-o-, -m-, or -p-chloronitrobenzene)(Î·6-cyclopentadienyl)iron cation of I (R = 2-, 3-, 4-O2N) with PhNH2, BuNH2, or pyrrolidine as nucleophile were investigated. Only selective displacement of the nitro group occurred for reactions with PhNH2. For reactions with BuNH2 or pyrrolidine, the o-isomer of I resulted in the selective displacement of only the chloro group, giving rise to the (Î·6-o-butylaminonitrobenzene)(Î·5-cyclopentadienyl)iron cation or the (Î·6-o-nitro-N-pyrrolidinylbenzene)(Î·5-cyclopentadienyl)iron cation, resp. With the m- or p-isomer of I, reaction with BuNH2 or pyrrolidine gave a mixt. of substitution products from competitive displacements of both chloro and nitro groups, the major product from the m-isomer being derived from displacement of the chloro group while the major product from the p-isomer resulted from displacement of the nitro group. Possible interpretations of these results are presented on the basis that the basicity of the nucleophile and the combined inductive effects of the nitro and chloro substituents would play important roles. [on SciFinder(R)]|
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