View PDF Version
 
DOI: 10.1039/A901698H (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1999, 2231-2236

New P–S–N containing ring systems. Reaction of 2,4-(naphthalene-1,8-diyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide with methylbis(trimethylsilyl)amine

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

Petr Kilián, Jaromír Marek, Radek Marek, Jaromír Tousek, Otakar Humpa, Alexandra M. Z. Slawin, Jirí Touzín, Josef Novosad and J. Derek Woollins

Abstract

From the reaction of 2,4-(naphthalene-1,8-diyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide 1 with methylbis(trimethylsilyl)amine 2 in dichloromethane a product of the P2S2 ring cleavage, (C10H6)P(S)(SSiMe3)(µ-S)P(S)(NMeSiMe3) 3, was isolated, existing in an equilibrium between two diastereomeric forms in solution. Compound 3 was also obtained when toluene was used as a solvent. Its subsequent reaction with pyridine (py) led to the desilylated ionic product [Hpy+][(C10H6)P(S)(NHMe)(µ-S)PS2–] 4, which reacts with tetraphenylphosphonium chloride to give [PPh4+][(C10H6)P(S)(NHMe)(µ-S)PS2–] 5. When acetonitrile was used as a solvent a cage compound 2,6-(naphthalene-1,8-diyl)-3,4-dimethyl-1,3,5,2λ5,6λ5-thiadiazadiphosphinine 2,6-disulfide 6 containing a six-membered CN2P2S heterocycle was obtained. The new compounds were studied spectroscopically (1- and 2-D high resolution NMR, IR, MS) and in the cases of 3, 5 and 6 by X-ray crystallography.

References

  1. W. Zeis, H. Henjes, D. Lux, W. Schwarz and H. Hess, Z. Naturforsch., Teil B, 1979, 34, 1334 Search PubMed.
  2. A. M. Z. Slawin, D. J. Williams, P. T. Wood and J. D. Woollins, J. Chem. Soc., Chem. Commun., 1987, 1741 RSC.
  3. M. R. St., J. Foreman, J. Novosad, A. M. Z. Slawin and J. D. Woollins, J. Chem. Soc., Dalton Trans., 1997, 1347 RSC.
  4. N. Walker and D. Stuart, Acta Crystallogr., Sect. A, 1983, 39, 158 CrossRef.
  5. KM4RED, data reduction program, KUMA Diffraction, Wroclaw, 1998.
  6. G. M. Sheldrick, SHELXS 86, University of Göttingen, 1986.
  7. G. M. Sheldrick, SHELXL 93, University of Göttingen, 1993.
  8. A. L. Davis, E. D. Laue, J. Keeler, D. Moskau and J. Lohman, J. Magn. Reson., 1991, 94, 637 CAS.
  9. J. Jeener, B. H. Meier, P. Bachmann and R. R. Ernst, J. Chem. Phys., 1979, 71, 4546 CrossRef CAS.
  10. A. Bax and M. F. Summers, J. Am. Chem. Soc., 1986, 108, 2093 CrossRef CAS.
  11. R. Marek, L. Králík and V. Sklenár, Tetrahedron Lett., 1997, 38, 665 CrossRef CAS.
  12. E. Pelaez-Arango, F. J. Garcia-Alonso, G. Carriedo and F. Lopez-Ortiz, J. Magn. Reson., Sect. A, 1996, 121, 154 Search PubMed.
  13. P. Kilián, J. Marek, R. Marek, J. Touzín, O. Humpa, J. Novosad and J. D. Woollins, J. Chem. Soc., Dalton Trans., 1998, 1175 RSC.
  14. R. Marek, O. Humpa and V. Sklenár, unpublished results.
  15. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902 CrossRef.
  16. H. W. Roesky and G. Remmers, Z. Anorg. Allg. Chem., 1977, 431, 221 CAS.
  17. M.-E. Eleftheriou, J. Novosad, D. J. Williams and J. D. Woollins, J. Chem. Soc., Chem. Commun., 1991, 116 RSC.
  18. P. Kilián, J. Touzín, J. Marek, J. D. Woollins and J. Novosad, Main Group Chem., 1996, 1, 425 Search PubMed.
  19. M. R. St., J. Foreman, A. M. Z. Slawin and J. D. Woollins, J. Chem. Soc., Chem. Commun., 1995, 2217 RSC.
  20. J. Breker and R. Schmutzler, Chem. Ber., 1990, 123, 1307 CAS; W. S. Sheldrick, S. Pohl, H. Zamankhan, M. Banek and D. Amirzadeh-Asl, Chem. Ber., 1981, 114, 2132 CAS; H. W. Roesky, K. Ambrosius, M. Banek and W. S. Sheldrick, Chem. Ber., 1980, 113, 1847 CAS; D. W. U. Schomburg and R. Schmutzler, Z. Naturforsch., Teil B, 1986, 41, 207 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.