View PDF Version
 
DOI: 10.1039/A906684E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 3637-3643

Diazadithiafulvalenes as electron donor reagents

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

Toshio Koizumi, Nadeem Bashir, Alan R. Kennedy and John A. Murphy

Abstract

Diazadithiafulvalenes act as excellent electron donors to arenediazonium salts. The diazadithiafulvalenium radical cations trap primary carbon radicals successfully. However, the diazadithiafulvalenium salts which form, undergo rapid ring fragmentation in contrast to their tetrathia counterparts.

References

  1. C. Lampard, J. A. Murphy and N. Lewis, J. Chem. Soc., Chem. Commun., 1993, 295 RSC.
  2. O. Callaghan, C. Lampard, A. R. Kennedy and J. A. Murphy, J. Chem. Soc., Perkin Trans. 1, 1999, 995 RSC.
  3. (a) G. V. Tormos, M. G. Bakker, P. Wang, M. V. Lakshmikantham, M. P. Cava and R. M. Metzger, J. Am. Chem. Soc., 1995, 117, 8528 CrossRef CAS; (b) G. V. Tormos, O. J. Neilands and M. P. Cava, J. Org. Chem., 1992, 57, 1008 CrossRef CAS.
  4. Preliminary communication: T. Koizumi, N. Bashir and J. A. Murphy, Tetrahedron Lett., 1997, 38, 7635 Search PubMed.
  5. H. W. Wanzlick, H.-J. Kleiner, I. Lasch, H. U. Füldner and H. Steinmaus, Liebigs Ann. Chem., 1967, 708, 155 Search PubMed.
  6. J. E. Baldwin and J. A. Walker, J. Am. Chem. Soc., 1974, 96, 596 CrossRef CAS.
  7. K. Yamaguchi, T. Itoh, K. Nagata, M. Okada and A. Ohsawa, Acta Crystallogr., Sect. C,, 1993, 49, 1514 CrossRef; T. Itoh, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron, 1993, 49, 4859 CrossRef CAS.
  8. B. Patro, A. R. Kennedy, O. Callaghan, X. Franck and J. A. Murphy, unpublished work.
  9. J.-J. Vorsanger, Bull. Soc. Chim. Fr., 1968, 971 CAS.
  10. S. Ghosh, S. R. Raychaudhuri and R. G. Salomon, J. Org. Chem., 1987, 52, 83 CrossRef CAS.
  11. J. A. Murphy, R. J. Fletcher, C. Lampard and N. Lewis, J. Chem. Soc., Perkin Trans. 1, 1995, 623 RSC.
  12. S. Raeppel, F. Raeppel and J. Suffert, Synlett, 1998, 7, 794.
  13. Crystal Data. A colourless block of C18H18N2O2S2 of approximate size 0.20 × 0.20 × 0.20 mm was mounted in oil on a Rigaku AFC7S diffractometer at 123 K. Monoclinic, space group P21/c, a= 11.4859(8), b= 9.0253(10), c= 16.4066(11)Å, β= 96.647(5)°, U= 1689.3(2)Å3, Z= 4. Measurements were made using λ= 0.71069 Å radiation and the ω/2θ method to a 2θmax of 55°. Of 4327 reflections, 4128 were unique (Rint= 0.033) and 2344 observed with I > 2σ(I). The structure was solved using direct methods14 and reflned to convergence on F15R= 0.047, Rw= 0.057 and S= 1.57 for 236 parameters. CCDC reference number 207/376. See http;//www.rsc.org/suppdata/p1/1999/3637/ for crystallographic files in .cif format.
  14. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori and M. Camalli, J. Appl. Crystallogr., 1994, 27, 435 CrossRef.
  15. Texsan, Version 1.6, Crystal Structure Analysis Package, Molecular Structure Corporation, The Woodlands, Texas 77381, 1992 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.