74032-61-4Relevant articles and documents
Unusual β,β′-coupling and β-alkylation of methyl 2,3,3-trifluoropropenoate by lithium diorganocuprates
Hajduch, Jan,Paleta, Old?ich
experimental part, p. 143 - 146 (2011/03/22)
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 β,β′ C,C-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.).
