Get access

Installation of Amine Moieties into a Polycyclic Anodic Product Derived from 2,4-Dimethylphenol

Authors

  • Joaquin Barjau,

    1. Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-26777
    Search for more papers by this author
  • Dr. Jan Fleischhauer,

    1. Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-26777
    Search for more papers by this author
  • Dr. Gregor Schnakenburg,

    1. Institute of Inorganic Chemistry, Friedrich-Wilhelms-University Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn (Germany)
    Search for more papers by this author
  • Prof. Dr. Siegfried R. Waldvogel

    Corresponding author
    1. Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-26777
    • Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10–14, 55128 Mainz (Germany), Fax: (+49) 6131-39-26777
    Search for more papers by this author

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.

Ancillary