title: Installation of amine moieties into a polycyclic anodic product derived from 2,4-dimethylphenol.
abstract: When 2,4-dimethylphenol is anodically treated, a dehydrotetramer with four contiguous stereocentres is readily obtained on a multi-gram scale. The substitution of a 2,4-dimethyl-phenoxy fragment by several amines was demonstrated, and the best results were obtained with primary amines. Optically pure α-chiral aliphatic amines yield diastereomeric mixtures that can be separated in most cases. The basic amine causes a partial hemiketal-opening of the bisbenzofuran moiety leading to an equilibrium within an α,β-unsaturated cyclohexenone. This dynamic behaviour occurs on the time scale of NMR spectroscopy and is also found by X-ray analysis providing a consistent picture.
authors: Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
authors: Joaquin
authors: J
authors: Barjau
authors: Jan
authors: J
authors: Fleischhauer
authors: Gregor
authors: G
authors: Schnakenburg
authors: Siegfried R
authors: SR
authors: Waldvogel