Synthesis, stereochemistry and decomplexation of ( η-arene)( η-cyclopentadienyl) iron(II) hexafluorophosphate complexes containing amino acid side chains. A route to N-arylamino acids

[( η-Substituted arene)( η-cyclopentadienyl)Fe][PF 6] complexes with amino acid side chains on the arene ring have been prepared by reaction of [( η-haloarene)( η-cyclopentadienyl)Fe][PF 6] complexes with amino acids and amino acid esters under various conditions. Evidence is presented from 1H- and...

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Bibliographic Details
Published in:Journal of organometallic chemistry 1997-10, Vol.544 (2), p.197-205
Main Authors: Roberts, Roger M.G., Johnsen, Emma
Format: Article
Language:English
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Summary:[( η-Substituted arene)( η-cyclopentadienyl)Fe][PF 6] complexes with amino acid side chains on the arene ring have been prepared by reaction of [( η-haloarene)( η-cyclopentadienyl)Fe][PF 6] complexes with amino acids and amino acid esters under various conditions. Evidence is presented from 1H- and 13C-NMR spectroscopy for the existence of conformational isomers resulting from restricted rotation about the arene-nitrogen bond. Where a chlorine substituent is also present in the complexed arene, diastereoisomers can be separated by column chromatography. Decomplexation of the complexes is reported in strongly basic media or using 1,8-phenanthroline in light-catalysed reactions offering a new route to N-arylamino acids.
ISSN:0022-328X
1872-8561
DOI:10.1016/S0022-328X(97)00292-1