PubMed Health⌕ Search

Biomedical subjects

Siegfried R Waldvogel

Publications and source records attributed to Siegfried R Waldvogel.

8 recordsLinked to original sources

Novel template-directed anodic phenol-coupling reaction.

Substituted phenols were anodically coupled to the corresponding 2,2'-biphenols via tetraphenoxy borate derivatives. This electrochemical method is particularly useful for methyl-substituted substrates, such as 2,4-dimethyl phenol. The selective ortho-coupling reaction can be easily performed on a multikilogram scale.

Borates↗

A supramolecular fluorescence probe for caffeine.

[structure: see text] Supramolecular sensing is rather limited to charged analytes. This report describes a practicable assay for caffeine, which employs a competitive "indicator-displacement" approach and allows detection by fluorescence. A simple analytical protocol is described that allows quantitation of caffeine in beverages.

Biosensing Techniques↗

Direct assignment of enantiofacial discrimination on single heterocyclic substrates by self-induced CD.

The first direct assignment of highly dynamic enantiofacial discrimination acting on a single heterocyclic substrate has been achieved by a combination of experimental and theoretical CD spectroscopy. The interaction of chirally modified hosts based on triphenylene ketals with appropriate prochiral guests can lead to the preferential formation of one diastereomeric host-guest complex. This reversible stereoselective binding transmits the chiral information from remote chiral groups in the host to the strongly absorbing triphenylene chromophore, which gives rise to self-induced CD. This effect was exploited for the determination of the enantiofacial recognition in various host-guest systems. Inversion of the steric demand either of the chiral substituents at the host or of the prochiral guest leads to almost complete inversion of the resulting CD spectra. For the assignment of the absolute stereochemistry of the complexes, a combined molecular dynamics/quantum-chemical approach was successfully employed. Despite the size and the highly dynamic character of the supramolecular systems, fundamental properties of the systems and details of the spectra were simulated accurately, providing access to fast and reliable assignment of the enantiofacial preference. The results are highly consistent with available X-ray data.

Journal Article↗

Dehydrodimerization of iodobenzenes to iodinated biaryls.

The molybdenum pentachloride-mediated oxidative coupling of iodo-substituted electron rich benzenes without the loss of the iodo-substituents is reported. The presented methodology is an environmentally friendly alternative to known thallium(III)- and lead(IV)-reagents. Even 2,2',6,6'-tetraiodobiphenyl derivatives are easily accessible.

Journal Article↗