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Unusual beta,beta'-coupling and beta-alkylation of methyl 2,3,3-trifluoropropenoate by lithium diorganocuprates
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SYSNO ASEP 0370023 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Unusual beta,beta'-coupling and beta-alkylation of methyl 2,3,3-trifluoropropenoate by lithium diorganocuprates Author(s) Hajduch, Jan (UOCHB-X) RID
Paleta, O. (CZ)Number of authors 2 Source Title Journal of Fluorine Chemistry. - : Elsevier - ISSN 0022-1139
Roč. 132, č. 2 (2011), s. 143-146Number of pages 4 s. Language eng - English Country CH - Switzerland Keywords trifluoropropenoate ; lithium diorganocuprates ; stereoselectivity Subject RIV CC - Organic Chemistry CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000287906200011 DOI 10.1016/j.jfluchem.2010.12.003 Annotation Methyl 2,3,3-trifluoroprop-2-enoate (1) reacts with lithium diorganocuprates in two ways, by fluorine substitution at C-3 with alkyl or aryl, or by beta,beta' CC-coupling. The reaction product was strongly dependent on the organyl structure: while dibutyl- or diphenylcuprate reacted by C-3 substitution, dimethylcuprate afforded the product of the coupling, dimethyl (Z,Z)-2,3,4,5-tetrafluorohexa-2,4-dienedioate (3). (Z)-Configuration is highly prevailing in 3-alkylated 2,3-difluoropropenoates (77-90% rel.). (C) 2010 Elsevier B.V. All rights reserved. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2012
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