Journal of Organometallic Chemistry p. 171 - 184 (1995)
Update date:2022-08-04
Topics:
Guennec, N.
Moinet, C.
Addition of tetraethylammonium cyanide to a solution of η5-cyclopentadienyl)(η6-arene)iron (1 +), in acetonitrile can be studied by voltammetry.With electron-withdrawing groups such as nitro, keto, sulfone, azo and azoxy bonded to the arene, the reaction occurs immediately and a wave resulting form oxidation of hexadienyl species is observed in the range 0-IV vs.SCE.Preparation of various hexadienyl compounds was achieved with good yields.In order to obtain ortho-substituted benzonitriles, electrochemical and chemical oxidations of hexadienyl complexes were compared.The best results were obtained with N-bromosuccinimide (NBS) and a demetallation generally occurs.A one-pot synthesis of benzonitrile compounds can be achieved after addition of cyanide ion and then NBS to a solution of (η5-cyclopentadienyl)(η6-arene) iron (1 +) in acetonitrile.
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