Regioselective Synthesis of Carbon- and Silicon-Bridged 2-(N,N-Dialkylamino)ethyl-Substituted Cyclopentadienes

Christian Müller; Peter Jutzi

doi:10.1055/s-2000-6341

Synthesis 2000; 2000(3): 389-394
DOI: 10.1055/s-2000-6341

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Regioselective Synthesis of Carbon- and Silicon-Bridged 2-(N,N-Dialkylamino)ethyl-Substituted Cyclopentadienes

Christian Müller^* , Peter Jutzi

^*Fakultät für Chemie der Universität Bielefeld, 33615 Bielefeld, Germany; Fax (+49) 52 11 06 60 26; E-mail: peter.jutzi@uni-bielefeld.de

Abstract

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[2-(N,N-Dialkylamino)ethyl]cyclopentadienes have been used for the synthesis of the novel amino-functionalized silicon- and carbon-bridged cyclopentadiene derivatives 3a-c, 7, 10 and 13a-c. The C-C and C-Si coupling reactions described here are regioselective leading exclusively to the formation of 1,3-disubstituted isomers, as proven by ¹H NMR spectroscopy. The bis-cyclopentadienes 3a-c, 7, 10 and 13a-c can be deprotonated to the corresponding dianionic species.

amino-functionalized cyclopentadienes - ansa-metallocenes - fulvenes - regioselectivity

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