Studies on nucleophilic substitution reactions with ...
|Title||Studies on nucleophilic substitution reactions with cyclopentadienyliron complexes of some chloroarenes and nitroarenes and syntheses of substituted arenes by demetalation of the substitution products.|
|Author(s)||A. Abd-El-Aziz, C. Lee, A. Piorko, R. Sutherland|
|Journal||Section Title: Organometallic and Organometalloidal Compounds, Journal of Organometallic Chemistry|
|Abstract||Nucleophilic substitution reactions with the cyclopentadienyliron (CpFe) complex of m- or p-Cl2C6H4 with carbanion nucleophiles derived from Et acetoacetate (EAA), dibenzoylmethane (DBM) or diacetylmethane gave only monosubstitution as previously obsd. for the CpFe complex of o-Cl2C6H4. Reaction of the CpFe complex of 2,6-dimethylchlorobenzene (I) or 2,6-dimethylnitrobenzene (II) with nucleophiles derived from NH3, Me2NH, BuNH2, EtOH, PhOH, pyrrolidine, o-thiocresol and EAA all gave SNAr products, without significant steric hindrance. However, no reaction was obsd. in reaction of I or II with DBM, suggesting that only with a bulky nucleophile such as that derived from DBM were steric hindrance effects sufficiently large to prevent an SNAr reaction with I or II. Pyrolytic sublimation of the various SNAr products caused decompn. in some cases, but in most instances, demetalation took place, giving substituted arenes. New substituted arenes prepd. in this way in the present work included RC6H4CN(Bz)2, (R = p-Me, o-, m-, and p-Cl) and 2,6-Me2C6H3Y [Y = Me(CH2)3NH, C2H5O, o-MeC6H4S]. [on SciFinder(R)]|
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