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Syntheses and Crystal Structures of Ferrocenoindenes

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Author(s): Klaus Wurst | Gerhard Laus | Michael R. Buchmeiser | Herwig Schottenberger

Journal: Crystals
ISSN 2073-4352

Volume: 3;
Issue: 1;
Start page: 141;
Date: 2013;
Original page

Keywords: ferrocene | ferrocenoindene | planar chiral | racemic crystal

ABSTRACT
Ferrocenoindenes display planar chirality and thus represent valuable ligands for asymmetric catalysis. Here, we report on the synthesis of novel 3-(1,1-dibromomethylene)ferroceno[1,2-a]indene, (Z)-3-(1-bromomethylene)-6-iodoferroceno[1,2-a]indene, and benzo[5,6-f]ferroceno[2,3,a]inden-1-one. Any application-oriented design of chiral catalysts requires fundamental knowledge about the ligands involved, not only in terms of atom-connectivity, but also in terms of their three-dimensional structure and steric demand. Therefore, the crystal structures of 2-ferrocenylbenzoic acid, ferroceno[1,2-a]indene, and (Z)-3-(1-bromomethylene)-6-iodoferroceno[1,2-a]indene have been determined. The bond-lengths that can be retrieved therefrom also allow for an estimation of the reactivity of the aryl-iodo, bromo-methylidene and dibromomethylidene moieties.
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