"On Water": Unique Reactivity of Organic Compounds in Aqueous Suspension

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,...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 44; no. 21; pp. 3275 - 3279
Main Authors Narayan, Sridhar, Muldoon, John, Finn, M. G., Fokin, Valery V., Kolb, Hartmuth C., Sharpless, K. Barry
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 20.05.2005
WILEY‐VCH Verlag
Wiley
Subjects
Alkenes - chemistry
Azo Compounds - chemistry
Bridged-Ring Compounds - chemistry
Chemistry
Chemistry, Multidisciplinary
click chemistry
cycloaddition
Epoxy Compounds - chemistry
interfaces
Ketones - chemistry
Molecular Structure
Naphthalenes - chemistry
Organic Chemicals - chemistry
Physical Sciences
Polycyclic Compounds - chemistry
rearrangement
Science & Technology
Suspensions - chemistry
Water - chemistry
interfaces
DIELS-ALDER REACTIONS
MECHANISM
click chemistry
TRANSITION-STATE
CLAISEN REARRANGEMENT
SOLVENT
HYDROPHOBIC INTERACTIONS
ACCELERATION
ORIGIN
cycloaddition
MEDIA
water chemistry
MICROHETEROGENEITY
rearrangement
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Summary: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.
Bibliography:istex:130009F418F8DB11CCC78467E3BABC9497178CB5
ark:/67375/WNG-XW2FT62F-F
ArticleID:ANIE200462883
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.
Medline
NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200462883