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

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.

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 

2 Binger P. Leininger S. Stannek J. Gabor B. Mynott R. Bruckmann J. Krüger C. Angew. Chem., Int. Ed. Engl.  1995,  34:  2227 

3a Tabellion F. Nachbauer A. Leininger S. Peters C. Regitz M. Preuss F. Angew. Chem. Int. Ed.  1998,  37:  1233 

3b Tabellion F. Peters C. Fischbeck U. Regitz M. Preuss F. Chem.-Eur. J.  2000,  6:  4558 

4 Gleiter R. Lange H. Binger P. Stannek J. Krüger C. Bruckmann J. Zenneck U. Kummer S. Eur. J. Inorg. Chem.  1998,  1619 

5a Nyulászi L. Veszprémi T. J. Phys. Chem.  1996,  100:  6456 

5b Hofmann M. v. Ragué Schleyer P. Regitz M. Eur. J. Org. Chem.  1999,  3291 

6 For a review see: Heydt H. Top. Curr. Chem.  2003,  223:  215 

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 

8 Peters C. Stutzmann S. Disteldorf H. Werner S. Bergsträßer U. Krüger C. Binger P. Regitz M. Synthesis  2000,  529 

9 Weidner S. PhD Thesis   University of Kaiserslautern; Germany: 2002. 

10 Zurmühlen F. Rösch W. Regitz M. Z. Naturforsch., B: Chem. Sci.  1985,  40:  1077 

11 Mack A. PhD Thesis   University of Kaiserslautern; Germany: 1998. 

12 Mack A. Bergsträßer U. Reiß GJ. Regitz M. Eur. J. Org. Chem.  1999,  587 

13 Allspach T. Regitz M. Becker G. Becker W. Synthesis  1986,  31 

14 Berger S. Braun S. Kalinowski H.-O. NMR-Spektroskopie von Nichtmetallen   Vol. 3:  Georg Thieme Verlag; Stuttgart, New York: 1993.  p.140 

15 Rösch W. Regitz M. Synthesis  1987,  689 

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 

17 Grundmann C. Dean JM. J. Org. Chem.  1965,  30:  2809 

18 Becker G. Z. Anorg. Allg. Chem.  1977,  430:  66 

19 Allspach T. PhD Thesis   University of Kaiserslautern; Germany: 1986. 

20 Rösch W. Vogelbacher U.-J. Allspach T. Regitz M. J. Organomet. Chem.  1986,  306:  39 

21 Rösch W. Regitz M. Angew. Chem. Int. Ed. Engl.  1984,  23:  900 

22 Schmidt T. PhD Thesis   University of Kaiserslautern; Germany: 2000. 

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: [phone]; E-mail: [e-mail]].

24 Sheldrick GM. SHELXS-97, Program for Crystal Structure Solution   University of Göttingen; Germany: 1990. 

25 Sheldrick GM. SHELXS-97, Program for Crystal Structure Refinement   University of Göttingen; Germany: 1997.