| Selenium-catalyzed halolactonization: nucleophilic activation of electrophilic halogenating reagents. | |
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MedLine Citation:
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PMID: 15575789 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Diphenyl diselenide catalyzes the halolactonization of unsaturated acids with N-halosuccinimides under mild conditions. The diselenide not only accelerates the reactions, but in some cases affords regiocontrol in favor of gamma-lactone products. Experiments show that the regioselectivity in favor of gamma-lactones is a result of kinetic rather than thermodynamic control. |
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Authors:
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Shelli R Mellegaard; Jon A Tunge |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 69 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2004 Dec |
Date Detail:
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Created Date: 2004-12-03 Completed Date: 2005-02-14 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 8979-81 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Kansas, Lawrence, KS 66045, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Catalysis Fatty Acids, Unsaturated / chemical synthesis*, chemistry Kinetics Lactones / chemical synthesis, chemistry* Molecular Structure Selenium / chemistry* Stereoisomerism Succinimides / chemical synthesis, chemistry* |
| Chemical | |
Reg. No./Substance:
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0/Fatty Acids, Unsaturated; 0/Lactones; 0/Succinimides; 7782-49-2/Selenium |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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