Skip to main content

Thank you for visiting You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.


On the threshold of stability

Carbenes are short-lived compounds containing a highly reactive carbon atom, which makes them difficult to study. A stabilized derivative may lead to new magnetic materials.

This is a preview of subscription content, access via your institution

Access options

Rent or buy this article

Get just this article for as long as you need it


Prices may be subject to local taxes which are calculated during checkout

Figure 1: Stabilization of carbenes.
Figure 2: Carbenes that can almost be bottled.


  1. Tomioka, H., Iwamoto, E., Itakura, H. & Hirai, K. Nature 412, 626–628 (2001).

    Article  CAS  Google Scholar 

  2. Doering, W. v. E., Buttery, R. G., Laughlin, R. G. & Chaudhuri, N. J. Am. Chem. Soc. 78, 3224 (1956).

    Article  CAS  Google Scholar 

  3. Igau, A., Grützmacher, H., Baceiredo, A. & Bertrand, G. J. Am. Chem. Soc. 110, 6463–6466 (1988).

    Article  CAS  Google Scholar 

  4. Arduengo, A. J. III, Harlow, R. L. & Kline, M. J. Am. Chem. Soc. 113, 361–363 (1991).

    Article  CAS  Google Scholar 

  5. Dixon, D. A., Dobbs, K. D., Arduengo, A. J. III & Bertrand, G. J. Am. Chem. Soc. 113, 8782–8785 (1991).

    Article  CAS  Google Scholar 

  6. Doetschman, D. C. & Hutchison, C. A. Jr J. Chem. Phys. 56, 3964–3982 (1972).

    Article  CAS  Google Scholar 

  7. Zimmerman, H. E. & Paskovich, D. H. J. Am. Chem. Soc. 86, 2149–2160 (1964).

    Article  CAS  Google Scholar 

  8. Wasserman, E. et al. J. Am. Chem. Soc. 93, 6335–6337 (1971).

    Article  CAS  Google Scholar 

  9. Hirai, K. & Tomioka, H. J. Am. Chem. Soc. 121, 10213–10214 (1999).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to Heinz D. Roth.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Roth, H. On the threshold of stability. Nature 412, 598–601 (2001).

Download citation

  • Issue Date:

  • DOI:


Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing