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Issue 14, 2007
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Aminoalkylferrocenyldichlorophosphanes: facile synthesis of versatile chiral starting materials

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Abstract

A series of racemic and optically pure aminoalkylferrocenyldichlorophosphanes has been prepared by reaction of phosphorus trichloride with the corresponding lithiated aminoalkylferrocene precursors. Crystal structures of racemic 1-dichlorophosphanyl-2-N,N-dimethylaminomethylferrocene, racemic 1-dichlorophosphanyl-2-N,N-dimethylaminomethyl-3-triphenylsilylferrocene and (S)-N,N-dimethyl-1-[(R)-2-(dichlorophosphanyl)ferrocenyl]ethylamine reveal short intramolecular N⋯P distances, which are suggestive of weak N → P dative bonds. The aminoalkylferrocenyldichlorophosphanes can be used for the preparation of the corresponding primary phosphanes, one of which was characterised by X-ray crystallography. Optically pure (R)-N,N-dimethyl-1-[(S)-2-(phosphanyl)ferrocenyl]ethylamine can easily be lithiated twice to give the first enantiomerically pure lithium–phosphorus closo cluster compound, which was also structurally characterised.

Graphical abstract: Aminoalkylferrocenyldichlorophosphanes: facile synthesis of versatile chiral starting materials

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Publication details

The article was received on 27 Nov 2006, accepted on 31 Jan 2007 and first published on 19 Feb 2007


Article type: Paper
DOI: 10.1039/B617257A
Citation: Dalton Trans., 2007,0, 1377-1382
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    Aminoalkylferrocenyldichlorophosphanes: facile synthesis of versatile chiral starting materials

    S. Tschirschwitz, P. Lönnecke and E. Hey-Hawkins, Dalton Trans., 2007, 0, 1377
    DOI: 10.1039/B617257A

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