Abstract
The title compound [(N,N-di-methyl-amino)-meth-yl]ferrocene, [Fe(C5H5)(C8H12N)], (1), is an inter-esting starting material for the synthesis of planar chiral 1,2-disubstituted ferrocenes, as demonstrated by the preparation of (R p,R p)-bis-{2-[(di-methyl-amino)-meth-yl]ferrocen-yl}di-methyl-silane, [Fe2(C5H5)2(C18H18N2Si)], (2), from the li-thia-ted derivative of 1. The configuration of the lithium compound is unchanged after the substitution reaction and the chirality is preserved in space group P212121. In both compounds, the Cp rings adopt eclipsed conformations. Hirshfeld surface analysis was used to investigate the inter-molecular inter-actions, and showed that H⋯H (van der Waals) inter-actions dominate in both structures with contact percentages of 83.9 and 88.4% for 1 and 2, respectively.
Highlights
In 1951, ferrocene was synthesized serendipitously (Kealy & Pauson, 1951) and one year later it was examined by X-ray crystallography (Fischer & Pfab, 1952)
The (R,S)-meso-compound of bis[dimethyl(aminomethyl)ferrocenyl]dimethylsilane was characterized by Roewer and co-workers using X-ray diffraction analysis and formed during the synthesis of dimethyldichlorosilane with two equivalents of the racemic lithiated N,N-dimethylaminomethylferrocene (Palitzsch et al, 1999)
We report the crystal structures of 1 and enantiomerically pure (Rp,Rp)-bis[dimethyl(aminomethyl)
Summary
In 1951, ferrocene was synthesized serendipitously (Kealy & Pauson, 1951) and one year later it was examined by X-ray crystallography (Fischer & Pfab, 1952). Another application is the kinetically controlled asymmetric synthesis of silicon-stereogenic methoxy silanes using a planar chiral ferrocene backbone based on 1. The (R,S)-meso-compound of bis[dimethyl(aminomethyl)ferrocenyl]dimethylsilane was characterized by Roewer and co-workers using X-ray diffraction analysis and formed during the synthesis of dimethyldichlorosilane with two equivalents of the racemic lithiated N,N-dimethylaminomethylferrocene (Palitzsch et al, 1999). We report the crystal structures of 1 and enantiomerically pure (Rp,Rp)-bis[dimethyl(aminomethyl)-
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