"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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| Published in | Angewandte Chemie International Edition Vol. 44; no. 21; pp. 3275 - 3279 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
20.05.2005
WILEY‐VCH Verlag Wiley |
| Subjects | |
| Online Access | Get full text |
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Muldoon, John Sharpless, K. Barry Fokin, Valery V. Kolb, Hartmuth C. Narayan, Sridhar Finn, M. G. |
| Author_xml | – sequence: 1 givenname: Sridhar surname: Narayan fullname: Narayan, Sridhar organization: Department of Chemistry and the Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-554-6738 – sequence: 2 givenname: John surname: Muldoon fullname: Muldoon, John organization: Department of Chemistry and the Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-554-6738 – sequence: 3 givenname: M. G. surname: Finn fullname: Finn, M. G. organization: Department of Chemistry and the Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-554-6738 – sequence: 4 givenname: Valery V. surname: Fokin fullname: Fokin, Valery V. organization: Department of Chemistry and the Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-554-6738 – sequence: 5 givenname: Hartmuth C. surname: Kolb fullname: Kolb, Hartmuth C. organization: Department of Chemistry and the Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-554-6738 – sequence: 6 givenname: K. Barry surname: Sharpless fullname: Sharpless, K. Barry email: sharples@scripps.edu organization: Department of Chemistry and the Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 619-554-6738 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/15844112$$D View this record in MEDLINE/PubMed |
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| Keywords | 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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| Notes | 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 |
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| Snippet | Water, the medium of choice: Many reactions, such as Claisen rearrangements (see scheme), are dramatically accelerated when performed in aqueous suspension... |
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| SubjectTerms | 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 |
| Title | "On Water": Unique Reactivity of Organic Compounds in Aqueous Suspension |
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