1361598-69-7Relevant academic research and scientific papers
Installation of amine moieties into a polycyclic anodic product derived from 2,4-dimethylphenol
Barjau, Joaquin,Fleischhauer, Jan,Schnakenburg, Gregor,Waldvogel, Siegfried R.
, p. 14785 - 14791 (2011)
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.
