Bis(Cyclopentadienyliron)arene complexes

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Title Bis(Cyclopentadienyliron)arene complexes: a new route to the synthesis and functionalization of polyaromatic ethers.
Author(s) A. Abd-El-Aziz, D. Schriemer, C. de Denus
Journal Section Title: Organometallic and Organometalloidal Compounds, Organometallics
Date 1994
Volume 13
Issue 1
Start page 374
End page 384
Abstract A new development in the chem. of arenes activated toward SNAr reactions by the cyclopentadienyliron (FeCp+) moiety is presented in this work. A class of diiron complexes of diphenoxybenzenes were prepd. in a highly efficient and very mild fashion. Dihydroxy arom. compds. served as dinucleophiles, allowing for the formation of the diiron complexes. This could be achieved in either a one- or two-step procedure. A wide variety of dinucleophiles were incorporated into this study, as well as a no. of FeCp+ activated arenes. These reactions are not inhibited by bulky substituents on either the dinucleophiles or activated arenes. The diiron complexes themselves could also undergo SNAr reactions, provided that the complexed arenes contained a chlorine substituent. This allowed for the functionalization of the complexes with species that could not be introduced indirectly in their syntheses. The carbon nucleophiles generated from Et cyanoacetate or (phenylsulfonyl)acetonitrile could be attached to the complexed ethers in this manner. The FeCp+ moieties were removed easily by photolytic demetalation which allowed for the recovery of a wide range of functionalized diphenoxybenzenes. This methodol. is advantageous over all those previously reported and should be a practical route to the synthesis of arom. ethers. [on SciFinder(R)]
DOI 10.1021/om00013a055
ISSN 0276-7333

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