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Installation of Amine Moieties into a Polycyclic Anodic Product Derived from 2,4‐Dimethylphenol
Author(s) -
Barjau Joaquin,
Fleischhauer Jan,
Schnakenburg Gregor,
Waldvogel Siegfried R.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102722
Subject(s) - moiety , amine gas treating , diastereomer , chemistry , cyclohexenone , yield (engineering) , organic chemistry , polymer chemistry , materials science , metallurgy
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.