Intramolecular macrocyclization of bis(5-methylthio-1,2-dithiole-3-thione)s with triethyl phosphite. A stereoselective route to macrocyclic (Z)-thioxodesaurines

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

Sandra Rudershausen, Hans-Jürgen Holdt, Helmut Reinke, Hans-Joachim Drexler, Joachim Teller and Manfred Michalik


Abstract

Intramolecular macrocyclizations of [oligo(oxyethylene)ethylenedithio]bridged bis(5-methylthio-1,2-dithiole-3- thione)s 5a and b with P(OEt)3 in p-xylene furnished the macrocyclic thioxodesaurin (Z)-6, thioxodesaurin (E)-7 and 1,3-dithiafulvene (E)-8, respectively.


References

  1. H. Bergreen, Ber. Dtsch. Chem. Ges., 1888, 21, 337 Search PubMed.
  2. P. Yates, D. R. Moore and T. R. Lynch, Can. J. Chem., 1971, 49, 1456 CAS.
  3. (a) T. R. Lynch, I. P. Mellor, S. C. Nyburg and P. Yates, Tetrahedron Lett., 1967, 373 CrossRef CAS; (b) J. A. Kapecki, J. E. Baldwin and I. C. Paul, J. Am. Chem. Soc., 1968, 90, 5800 CrossRef CAS; (c) G. Lábbe, P. Vangheluwe, S. Toppet, G. S. D. King and L. Van Meervelt, Bull. Soc. Chim. Belg., 1984, 93, 405 CAS; (d) E. Schaumann, S. Scheiblich, U. Wriede and G. Adiwidjaja, Chem. Ber., 1988, 121, 1165 CAS.
  4. H. Meier and N. Hanold, Methoden Org. Chem., Houben-Weyl, 4th edn., 1985, vol. E11/2, pp. 1584–1597 Search PubMed.
  5. J. Amzil, J.-M. Catel, G. LeCoustumer, Y. Mollier and J.-P. Sauve, Bull. Soc. Chim. Fr., 1988, 101 CAS.
  6. G. Steimecke, H.-J. Sieler, R. Kirmse, W. Dietzsch and E. Hoyer, Phosphorus Sulfur, 1982, 12, 237 Search PubMed.
  7. (a) S. Rudershausen, H.-J. Drexler, H. Reinke, A. Knöchel and H.-J. Holdt, Sulfur Lett., 1995, 18, 233 Search PubMed; (b) S. Rudershausen, H.-J. Holdt and H.-J. Drexler, unpublished work.
  8. C. O. Kappe, C. T. Pedersen, J.-M. Catel and Y. Mollier, J. Chem. Soc., Perkin Trans. 2, 1994, 351 RSC.
  9. K. Hartke, N. Rettberg, D. Dutta and H.-D. Gerber, Liebigs Ann. Chem., 1993, 1081 Search PubMed.
  10. A. N. Mirskova, G. G. Levkovskaya, I. D. Kalikham, T. I. Vakulśkaya, V. A. Pestunovich and M. G. Voronkov, Izv. Akad. Nauk. SSSR, Ser. Khim., 1976, 2040 (Chem. Abstr., 1977, 86, 106439r) Search PubMed See also areview on thioketenes: E. Schaumann, Tetrahedron, 1988, 44, 1827 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.