New Aspects of Synthesis and Properties of Arylated Cyclopentadienes

Author: Dyker, Gerald; Heiermann, Jorg; Miura, Masahiro

Description: The multifold palladium-catalysed arylation is a suitable method for the synthesis of sterically crowded cyclopentadienes bearing up to five ortho-substituted aryl groups. A maximum of four mesitylene groups can be introduced. While penta(para-xylyl)cyclopentadiene and pentakis(2-chlorophenyl)cyclopentadiene exhibit at least six rotamers in the proton NMR spectrum, only two rotamers are registered for the tetra(2-chlorophenyl)cyclopentadiene; the all-trans isomer is identified as the major one both by spectroscopy and by semi-empirical calculations.

Subject headings: CH activation; Cyclopentadienes; Palladium catalysis; Rotamers

Publication year: 2003

Journal or book title: Advanced Synthesis & Catalysis

Volume: 345

Issue: 9-10

Pages: 1127-1132

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Serial number: 3356

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