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Organic chemistry

Stabilizers cause instability

Any chemist will tell you that amide compounds are renowned for their stability, yet a family of amides has been discovered that is surprisingly unstable. The cause of this phenomenon is even more surprising.

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Figure 1: Amide reactivity.


  1. Hutchby, M. et al. Angew. Chem. Int. Edn 51, 548–551 (2012).

    CAS  Article  Google Scholar 

  2. Snieckus, V. Chem. Rev. 90, 879–933 (1990).

    CAS  Article  Google Scholar 

  3. Clayden, J., Foricher, Y. J. Y. & Lam, H. K. Chem. Commun. 2138–2139 (2002).

  4. Clayden, J., Foricher, Y. J. Y. & Lam, H. K. Eur. J. Org. Chem. 3558–3565 (2002).

  5. Clayden, J. & Moran, W. J. Angew. Chem. Int. Edn 45, 7118–7120 (2006).

    CAS  Article  Google Scholar 

  6. Szostak, M. & Aubé, J. Org. Biomol. Chem. 9, 27–35 (2011).

    CAS  Article  Google Scholar 

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Correspondence to Jonathan Clayden.

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Clayden, J. Stabilizers cause instability. Nature 481, 274–275 (2012).

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