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Organic chemistry

Single molecules put a ring on it

A variant of a classical reaction has been used to generate short-lived chemical species called arynes, allowing the one-step synthesis of structurally complex benzene derivatives from simple precursors. See Article p.208

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Figure 1: Methods for preparing arynes.
Figure 2: A fresh twist on the Diels–Alder reaction.

References

  1. Hoye, T. R., Baire, B., Niu, D. Willoughby, P. H. & Woods, B. P. Nature 490, 208–212 (2012).

    Article  ADS  CAS  Google Scholar 

  2. Roberts, J. D. et al. J. Am. Chem. Soc. 75, 3290–3291 (1953).

    Article  CAS  Google Scholar 

  3. Kitamura, T. Aust. J. Chem. 63, 987–1001 (2010).

    Article  CAS  Google Scholar 

  4. Himeshima, Y., Sonoda, T. & Kobayashi, H. Chem. Lett. 12, 1211–1214 (1983).

    Article  Google Scholar 

  5. Tadross, P. M. & Stoltz, B. M. Chem. Rev. 112, 3550–3577 (2012).

    Article  CAS  Google Scholar 

  6. Diels, O. & Alder, K. J. Liebigs Ann. Chem. 460, 98–122 (1928).

    Article  CAS  Google Scholar 

  7. Nicolaou, K. C. et al. Angew. Chem. Int. Edn 41, 1668–1698 (2002).

    Article  CAS  Google Scholar 

  8. Cahill, K. J., Ajaz, A. & Johnson, R. P. Aust. J. Chem. 63, 1007–1012 (2010).

    Article  CAS  Google Scholar 

  9. Kawano, T., Inai, H., Miyawaki, K. & Ueda, I. Tetrahedron Lett. 46, 1233–1236 (2005).

    Article  CAS  Google Scholar 

Download references

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Correspondence to Sarah E. Reisman.

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Yeoman, J., Reisman, S. Single molecules put a ring on it. Nature 490, 179–180 (2012). https://doi.org/10.1038/490179a

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