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Synthesis of Terminal-Biradical Compounds Consisting of Two N-Oxyl Groups Connected with Conjugated π-Systems

  • Sigeru Torii
  • Tomoyuki Hase
  • Manabu Kuroboshi
  • Toshimasa Katagiri
  • Christian Amatore
  • Anny Jutand
  • Hiroyuki Kawafuchi
Conference paper

Abstract

The design and synthesis of molecular magnets are one of the current interests. Essentials are how to increase the spin density and to regulate the direction of the spins. For latter purpose, the radicals are attempted to be joined by π-electron systems to allow to interact each other. Poly-radical compounds connecting the radicals by aromatic structure are reported. However, the overlap with aromatic ring seems not efficient because of a steric repulsion. We planed to connect radicals by other type of rz­system, e.g., acetylenic and vinylic moieties. Herein, we describe synthetic results on terminal-biradical compounds 1 containing two N-oxyl groups connected with conjugated π-systems (Scheme 1) by (1) addition of magnesium acetylide to 4-oxo-TEMPO derivatives 2 followed by dehydration (Route A). or (2) Pd-catalyzed cross-coupling between acetylene derivatives and vinyl triflate 4 derived from 2 (Route B).1 The vinyl triflate 4 was found to be a potent intermediate to synthesize a variety of biradical compounds 1.

Keywords

Aromatic Structure Steric Repulsion Molecular Magnet Potent Intermediate Acetylene Derivative 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Reference

  1. S. Torii, et al., Tetrahedron Lett. 1997, 38,7391.Google Scholar

Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Sigeru Torii
    • 2
  • Tomoyuki Hase
    • 1
  • Manabu Kuroboshi
    • 1
  • Toshimasa Katagiri
    • 1
  • Christian Amatore
    • 2
  • Anny Jutand
    • 2
  • Hiroyuki Kawafuchi
    • 2
  1. 1.Department of Applied Chemistry, Faculty of EngineeringOkayama UniversityOkayama 700Japan
  2. 2.Ecole Normal Superieure, Departoment de ChimieURA CNRS 1679Paris Cedex 05France

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