Iron cyclopentadienyl mediated ...

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Title Iron cyclopentadienyl mediated 2-alkyl-2-arylphenylsulfonylacetonitrile synthesis.
Author(s) Alaa S. Abd-El-Aziz, Christine R. de Denus, Harold M. Hutton
Journal Section Title: Benzene, Its Derivatives, and Condensed Benzenoid Compounds, Canadian Journal of Chemistry
Date 1995
Volume 73
Issue 2
Start page 289
End page 295
Abstract A unique route to the synthesis of 2-alkyl-2-arylphenylsulfonylacetonitriles via the nucleophilic arom. substitution (SNAr) of (chloroarene)cyclopentadienyliron complexes with 2-alkyl phenylsulfonylacetonitriles was studied. Reactions of chloroarene complexes with 2-alkyl phenylsulfonylacetonitrile in the presence of K2CO3 in DMF at room temp. gave I (R1 = H, o-, m-, p-Me; R2 = Et, Bu) in good yields. The use of alkylated phenylsulfonylacetonitriles as nucleophiles in the reactions with the p-dichlorobenzene complex gave I (R1 = CR2(CN)(SO2Ph), R2 = Et, Bu). Photolytic demetalation provided an efficient route to the liberation of the arylated phenylsulfonylacetonitriles. [on SciFinder(R)]

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