| (beta-Trifluoromethyl)Vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds. | |
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MedLine Citation:
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PMID: 21797270 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Two trifluoromethyl-substituted building block (beta-trifluoromethyl)vinyl sulfonium salts 1 and 2 were developed. Reactions of (beta-trifluoromethyl)vinyl sulfonium salt 1 with active methylene compounds containing electron-withdrawing groups using DBU as the base in DMSO occurred to give trifluoromethyl-substituted cyclopropane derivatives 7 as the major products. In contrast, reactions of (beta-trifluoromethyl)vinyl sulfonium salt 2 with active methylene compounds occurred with the migration of one of the electron-withdrawing groups to give the products 8 as the major products when NaH was used as the base in DMSO. Moreover, when NaH was used as base in THF/CH2Cl2 at -78 degrees C, reactions of both (beta-trifluoromethyl)vinyl sulfonium salts 1 and 2 gave trifluoromethyl-substituted 2,3-dihydrofuran derivatives 9 as the major products. A working mechanism was proposed to explain the different behaviors of the beta-trifluoromethyl-substituted vinylsulfoniums 1 or 2 with active methylene compounds under these different conditions. |
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Authors:
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Hao Lin; Qilong Shen; Long Lu |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-7-28 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: - Publication Date: 2011 Jul |
Date Detail:
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Created Date: 2011-7-29 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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