Skip to main content
SpringerLink
Log in

Reaction of stannenes and phosphastannenes with aldehydes and ketones: New tin four-membered ring derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Stannene Tip2Sn=CR2 1 (Tip=2,4,6-triisopropylphenyl, CR2=fluorenylidene) enters a [2+2] cycloaddition reaction with benzophenone to afford the four-membered ring derivative2. This stannaoxetane undergoes a [2+2] decomposition with formation of the corresponding stannanone8 and alkene9 and an easy hydrolysis by initial cleavage of the Sn−C bond. Diphenylacetaldehyde also gives with1 a stannaoxetane, which has been characterized by its hydrolysis products. Phosphastannene Tip2Sn=PAr13 (Ar=2,4,6-tri-tert-butylphenyl) reacts with benzaldehyde according to a [2+2] cycloaddition pattern leading to stannaphosphaoxetane14, whereas ene-products19–21 were obtained with acetaldehyde, acetone, and acetophenone.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. G. Raabe and J. Michl,Chem. Rev.,85, 419 (1985).

    Article  Google Scholar 

  2. A. G. Brook and M. A. Brook,Adv. Organomet. Chem.,39, 71 (1996).

    Google Scholar 

  3. R. West,Angew. Chem. Int. Ed. Engl.,26, 1201 (1987).

    Article  Google Scholar 

  4. M. Weidenbruch,Coord. Chem. Rev.,130, 275 (1994).

    Article  Google Scholar 

  5. I. Hemme and U. Klingebiel,Adv. Organomet. Chem.,39, 159 (1996).

    Google Scholar 

  6. R. Okazaki and R. West,Adv. Organomet. Chem.,39, 232 (1996).

    Google Scholar 

  7. M. Driess,Adv. Organomet. Chem.,39, 193 (1996).

    Google Scholar 

  8. G. Raabe and J. Michl, in:The Chemistry of Organic Silicon Compounds, S. Patai, Z. Rappoport (eds.), Wiley, New York (1989).

    Google Scholar 

  9. M. A. Chaubon, H. Ranaivonjatovo, J. Escudié, and J. Satgé,Main Group Met. Chem.,19, 145 (1996).

    Google Scholar 

  10. A. Kandri Rodi, H. Ranaivonjatovo, J. Escudié, and A. Kerbal,Main Group Met. Chem.,19, 199 (1996).

    Google Scholar 

  11. T. Tsumuraya, S. A. Batcheller, and S. Masamune,Angew. Chem. Int. Ed. Engl.,30, 902 (1991).

    Article  Google Scholar 

  12. N. Tokitoh and R. Okazaki,Main Group Chem. News.,3, 4 (1995).

    Google Scholar 

  13. K. M. Baines and W. G. Stibbs,Adv. Organomet. Chem.,39, 275 (1996).

    Google Scholar 

  14. J. Barrau, J. Escudié, and J. Satgé,Chem. Rev.,90, 283 (1990).

    Article  Google Scholar 

  15. J. Escudié, C. Couret, H. Ranaivonjatovo, and J. Satgé,Coord. Chem. Rev.,130 427 (1994).

    Article  Google Scholar 

  16. G. Ossig, A. Meller, S. Freitag, R. Herbst-Irmer, and G. M. Sheldrick,Chem. Ber.,126, 2247 (1993).

    Google Scholar 

  17. G. Anselme, H. Ranaivonjatovo, J. Escudié, and C. Couret, J. Satgé,Organometallics.,11, 2748 (1992).

    Article  Google Scholar 

  18. G. Anselme, J.-P. Declercq, A. Dubourg, H. Ranaivonjatovo, J. Escudié, and C. Couret,J. Organomet. Chem.,458, 49 (1993).

    Article  Google Scholar 

  19. N. Wiberg and C.-K. Kim,Chem. Ber.,119, 2980 (1986).

    Google Scholar 

  20. M. Lazraq, C. Couret, J. Escudié, J. Satgé, and M. Draeger,Organometallics.,10, 1771 (1991).

    Article  Google Scholar 

  21. A. D. Fanta, D. J. De Young, J. Belzner, and R. West,Organometallics,10, 3466 (1991).

    Article  Google Scholar 

  22. G. Delpon-Lacaze, C. Couret, J. Escudié, and J. Satgé,Main Group Met. Chem.,16, 419 (1993).

    Google Scholar 

  23. N. Wiberg, G. Preiner, K. Schurz, and G. Fischer,Z. Naturforsch. B. Chem. Sci.,43, 1468 (1988).

    Google Scholar 

  24. A. G. Brook, W. J. Chatterton, J. F. Sawyer, D. W. Hughes, and K. Vorspohl,Organometallics.,6, 1246 (1987).

    Article  Google Scholar 

  25. G. Wittig and H. Laib,Liebigs Ann. Chem.,580, 57 (1953).

    Google Scholar 

  26. H. Ranaivonjatovo, J. Escudié, C. Couret, and J. Satgé,J. Chem. Soc. Chem. Comm., No. 15, 1047 (1992).

    Article  Google Scholar 

  27. H. Ranaivonjatovo, J. Escudié, C. Couret, and J. Satgé,J. Organomet. Chem.,415, 327 (1991).

    Article  Google Scholar 

  28. A. Kandri Rodi, H. Ranaivonjatovo, and J. Escudié,Organometallics.,13, 2787 (1994).

    Article  Google Scholar 

  29. M. J. Fink, D. J. De Young, R. West, and J. Michl,J. Amer. Chem. Soc.,105, 1070 (1983).

    Article  Google Scholar 

  30. S. A. Batcheller and S. Masamune,Tetrah. Lett.,29, 3383 (1988).

    Article  Google Scholar 

  31. S. Masamune and L. R. Sita,J. Amer. Chem. Soc.,107, 6390 (1985).

    Article  Google Scholar 

  32. B. Glaser and H. Noth,Chem. Ber.,119, 3856 (1986).

    Google Scholar 

  33. G. Wittig and G. Pieper,Liebigs Ann. Chem.,558, 207 (1947).

    Google Scholar 

  34. M. Luisa, T. M. B. Franco, B. J. Herold, J. C. Evans, and C. C. Rowlands,J. Chem. Soc. Perkin Trans., II, No. 4, 443 (1988).

    Google Scholar 

Download references

Authors
  1. A. Kandri Rodi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. Anselme
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. H. Ranaivonjatovo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. J. Escudié
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Hétérochimie Fondamentale et Appliquée, UPRES A 5069, Université Paul Sabatier, 31062 Toulouse cedex 04, France. Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2022, Fčs-Saiss, Fčs, Maroc. Laboratoire de Synthčse Organique, Faculté des Sciences, 40 Avenue du Recteur Pineau, 86022 Poitiers, France. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp 1098–1106, August, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rodi, A.K., Anselme, G., Ranaivonjatovo, H. et al. Reaction of stannenes and phosphastannenes with aldehydes and ketones: New tin four-membered ring derivatives. Chem Heterocycl Compd 35, 965–972 (1999). https://doi.org/10.1007/BF02252165

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02252165

Keywords

Search

Navigation