Unusual beta,beta'-coupling and beta-alkylation of methyl 2,3,3-trifluoropropenoate by lithium diorganocuprates

0370023 - ÚOCHB 2012 RIV CH eng J - Článek v odborném periodiku
Hajduch, Jan - Paleta, O.
Unusual beta,beta'-coupling and beta-alkylation of methyl 2,3,3-trifluoropropenoate by lithium diorganocuprates.
Journal of Fluorine Chemistry. Roč. 132, č. 2 (2011), s. 143-146. ISSN 0022-1139. E-ISSN 1873-3328
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: trifluoropropenoate * lithium diorganocuprates * stereoselectivity
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.033, rok: 2011

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.
Trvalý link: http://hdl.handle.net/11104/0203943