Transylidation of a transiently formed nitrilium phosphane ylide complex

(Note: The full text of this document is currently only available in the PDF Version )

Hendrik Wilkens, Frank Ruthe, Peter G. Jones and Rainer Streubel


Abstract

Thermal decomposition of the 3-phenyl-substituted 2H-azaphosphirene complex 1 in the presence of dimethyl cyanamide and dimethyl acetylenedicarboxylate (DMAD) yielded dimethylamino-substituted products, the 2H-1,2- azaphosphole complex 4b and the diastereoisomeric Δ3-1,3,2-oxazaphospholene complexes 5a,b; this represents the first example of 1,3-dipolar cycloaddition reactions of a nitrilium phosphane ylide complex that is generated in situ by transylidation.


References

  1. A. Ostrowski, J. Jeske, P. G. Jones and R. Streubel, J. Chem. Soc., Chem. Commun., 1995, 2507 RSC.
  2. R. Streubel, H. Wilkens, A. Ostrowski, C. Neumann, F. Ruthe and P. G. Jones, Angew. Chem., Int. Ed. Engl., 1997, 36, 1492 CrossRef CAS.
  3. H. Wilkens, J. Jeske, P. G. Jones and R. Streubel, Chem. Commun., 1997, 2317 RSC.
  4. R. K. Howe and J. E. Franz, J. Org. Chem., 1974, 39, 962 CrossRef CAS.
  5. A. Padwa, 1,3-Dipolar Cycloaddition Chemistry, Wiley, New York, 1984 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.