Nucleophilic substitution reactions of ...



Title Nucleophilic substitution reactions of η6-o-dichlorobenzene-η5-cyclopentadienyliron hexafluorophosphate.
Author(s) C. C. Lee, A. S. Abd-el-Aziz, R. L. Chowdhury, U. S. Gill, A. Piorko, R. G. Sutherland
Journal Section Title: Organometallic and Organometalloidal Compounds, Journal of Organometallic Chemistry
Date 1986
Volume 315
Issue 1
Start page 79
End page 92
Abstract Reaction of [(η6-o-Cl2C6H4)Fe(η5-C5H5)][PF6] (I) with an excess of PhOH or p-MeC6H4SH in the presence of K2CO3 gave disubstitution of both chloro groups of I, whereas a similar reaction with one equiv of the nucleophile under conditions of high diln. gave monosubstitution of one of the chloro groups of I. Similarly, di- or monosubstitution occurred with PhCH2OH or MeOH as the source of the nucleophile. A reaction occurred between I and o-MeOC6H4NH2 (II), but only the monosubstitution product was obtained, even in the presence of an excess of II. Monosubstitution was obsd. with other nucleophiles contg. the NH2 group, including NH3, NH2NH2, MeNH2 and PhCH2NH2. Reaction between I and the carbanion-enolate anion derived from acetylacetone, α-benzoylacetophenone, diethyl malonate or ethyl acetoacetate gave monosubstitution of one of the chloro groups leading to the formation of a C-C bond. An explanation for formation of monosubstitution products in reactions with N- or C-contg. nucleophiles was discussed. [on SciFinder(R)]
DOI 10.1016/0022-328X(86)80413-2

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