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Synthesis 2004(2): 241-248  
DOI: 10.1055/s-2004-44384
PAPER
© Georg Thieme Verlag Stuttgart · New York

Organophosphorus Compounds, Part 168; [1] 1,3-Dipolar Cycloaddition Reactions of 1,3,5-Triphosphinines with Nitrile Oxides

Steffen Weidner, Jens Renner, Uwe Bergsträßer, Manfred Regitz*, Heinrich Heydt*
Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Straße, 67663 Kaiserslautern, Germany
Fax: +49(631)2053921; e-Mail: heydt@chemie.uni-kl.de;
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Publication History

Received 26 February 2003
Publication Date:
18 December 2003 (online)

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Abstract

Phenylnitrile oxide as well as mesitylnitrile oxide underwent 1,3-dipolar cycloaddition reactions with the 1,3,5-triphosphinines 2 under mild conditions to furnish the condensed heterocyclic compounds 9 and 11, respectively. Oxadiphospholes 14 were accessible by fragmentation reactions of 11.

Key words

phosphorus - 1,3-dipolar cycloadditions - nitrile oxides - 1,2,4-oxazaphospholes - 1,2,4-oxadiphospholes

    References

  • 1 Part 167, see: Dietz J. Bergsträßer U. Binger P. Regitz M. Eur. J. Org. Chem.  2003,  512 
    CrossrefGoogle Scholar
  • 2 Binger P. Leininger S. Stannek J. Gabor B. Mynott R. Bruckmann J. Krüger C. Angew. Chem., Int. Ed. Engl.  1995,  34:  2227 
    CrossrefGoogle Scholar
  • 3a Tabellion F. Nachbauer A. Leininger S. Peters C. Regitz M. Preuss F. Angew. Chem. Int. Ed.  1998,  37:  1233 
    Google Scholar
  • 3b Tabellion F. Peters C. Fischbeck U. Regitz M. Preuss F. Chem.-Eur. J.  2000,  6:  4558 
    Google Scholar
  • 4 Gleiter R. Lange H. Binger P. Stannek J. Krüger C. Bruckmann J. Zenneck U. Kummer S. Eur. J. Inorg. Chem.  1998,  1619 
    CrossrefGoogle Scholar
  • 5a Nyulászi L. Veszprémi T. J. Phys. Chem.  1996,  100:  6456 
    CrossrefGoogle Scholar
  • 5b Hofmann M. v. Ragué Schleyer P. Regitz M. Eur. J. Org. Chem.  1999,  3291 
    CrossrefGoogle Scholar
  • 6 For a review see: Heydt H. Top. Curr. Chem.  2003,  223:  215 
    Google Scholar
  • 7 Peters C. Disteldorf H. Fuchs E. Werner S. Stutzmann S. Bruckmann J. Krüger C. Binger P. Heydt H. Regitz M. Eur. J. Org. Chem.  2001,  3425 
    CrossrefGoogle Scholar
  • 8 Peters C. Stutzmann S. Disteldorf H. Werner S. Bergsträßer U. Krüger C. Binger P. Regitz M. Synthesis  2000,  529 
    Article in Thieme ConnectGoogle Scholar
  • 9 Weidner S. PhD Thesis   University of Kaiserslautern; Germany: 2002. 
    Google Scholar
  • 10 Zurmühlen F. Rösch W. Regitz M. Z. Naturforsch., B: Chem. Sci.  1985,  40:  1077 
    Google Scholar
  • 11 Mack A. PhD Thesis   University of Kaiserslautern; Germany: 1998. 
    Google Scholar
  • 12 Mack A. Bergsträßer U. Reiß GJ. Regitz M. Eur. J. Org. Chem.  1999,  587 
    CrossrefGoogle Scholar
  • 13 Allspach T. Regitz M. Becker G. Becker W. Synthesis  1986,  31 
    Article in Thieme ConnectGoogle Scholar
  • 14 Berger S. Braun S. Kalinowski H.-O. NMR-Spektroskopie von Nichtmetallen   Vol. 3:  Georg Thieme Verlag; Stuttgart, New York: 1993.  p.140 
    Google Scholar
  • 15 Rösch W. Regitz M. Synthesis  1987,  689 
    Article in Thieme ConnectGoogle Scholar
  • 16 The nitrile oxide was prepared in situ from N-hydroxy-benzenecarboximidoyl chloride by elimination of HCl with triethylamine in Et2O: Weiland H. Ber. Dtsch. Chem. Ges.  1907,  40:  1670 
    Google Scholar
  • 17 Grundmann C. Dean JM. J. Org. Chem.  1965,  30:  2809 
    CrossrefGoogle Scholar
  • 18 Becker G. Z. Anorg. Allg. Chem.  1977,  430:  66 
    CrossrefGoogle Scholar
  • 19 Allspach T. PhD Thesis   University of Kaiserslautern; Germany: 1986. 
    Google Scholar
  • 20 Rösch W. Vogelbacher U.-J. Allspach T. Regitz M. J. Organomet. Chem.  1986,  306:  39 
    CrossrefGoogle Scholar
  • 21 Rösch W. Regitz M. Angew. Chem. Int. Ed. Engl.  1984,  23:  900 
    CrossrefGoogle Scholar
  • 22 Schmidt T. PhD Thesis   University of Kaiserslautern; Germany: 2000. 
    Google Scholar
  • 24 Sheldrick GM. SHELXS-97, Program for Crystal Structure Solution   University of Göttingen; Germany: 1990. 
    Google Scholar
  • 25 Sheldrick GM. SHELXS-97, Program for Crystal Structure Refinement   University of Göttingen; Germany: 1997. 
    Google Scholar
23

Crystal data (excluding structure factors) for the structure reported in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-211047. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [Fax: +44(1223)336033; E-mail: deposit@chemcrys.cam.ac.uk].