Arylation of diethyl alkylmalonates: synthetic route ...
|Title||Arylation of diethyl alkylmalonates: synthetic route to diethyl alkyl(substituted aryl)malonates with the aid of temporary arene complexation by the cyclopentadienyliron moiety.|
|Author(s)||A. Piorko, A. Abd-El-Aziz, C. Lee, R. Sutherland|
|Journal||Section Title: Organometallic and Organometalloidal Compounds, Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999)|
|Abstract||Nucleophilic substitution of Cl in the cyclopentadienyliron hexafluorophosphates of chlorobenzene, isomeric chlorotoluenes and dichlorobenzenes I (Cp = cyclopentadienyl, R1 = o-, p-Me, -Cl, m-Cl) with the anions generated from di-Et alkylmalonates R2CH(CO2Et)2 (R2 = Me, Et) leads to the formation of cyclopentadienyliron complexes II. An excess of the anion employed in reactions with the m- and p-dichlorobenzene complexes leads to substitution of both Cl atoms and formation of isomeric phenylenedimalonate complexes II [R1 = CEt(CO2Et)2]. Malonyl cations II possessing a chloro substituent on the complexed Ph ring provide the possibility of further modifications of Ph ring substituents via substitution [e.g. III] or addn. reactions. The described complexes have been demetalated giving di-Et alkyl(substituted phenyl)malonates in >50% overall yield from I. [on SciFinder(R)]|
Using APA 6th Edition citation style.
Times viewed: 84