We thank Dr. Vladislav Litosh for carrying out preliminary work. Support from the National Institutes of Health, National Institute of General Medical Sciences (GM 28384), the National Science Foundation (CHE9985553), the Skaggs Institute for Chemical Biology, and the W. M. Keck Foundation is gratefully acknowledged. S.N. thanks the Skaggs Institute for a postdoctoral fellowship. We also thank Dr. Suresh Suri, Edwards Air Force Base, California, for a generous gift of quadricyclane. We urge our fellow chemists to float their problematic reactions on water and to send observations of success or failure to us at onwater@scripps.edu for public dissemination with attribution.
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Communication
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“On Water”: Unique Reactivity of Organic Compounds in Aqueous Suspension†
Article first published online: 21 APR 2005
DOI: 10.1002/anie.200462883
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Narayan, S., Muldoon, J., Finn, M. G., Fokin, V. V., Kolb, H. C. and Sharpless, K. B. (2005), “On Water”: Unique Reactivity of Organic Compounds in Aqueous Suspension. Angew. Chem. Int. Ed., 44: 3275–3279. doi: 10.1002/anie.200462883
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Publication History
- Issue published online: 17 MAY 2005
- Article first published online: 21 APR 2005
- Manuscript Received: 10 DEC 2004
Keywords:
- click chemistry;
- cycloaddition;
- interfaces;
- rearrangement;
- water chemistry
Water, the medium of choice: Many reactions, such as Claisen rearrangements (see scheme), are dramatically accelerated when performed in aqueous suspension (“on water”) relative to organic solvents or even neat conditions. Low miscibility of organic compounds with water is not detrimental: in fact, it facilitates the isolation of products.