160564-37-4Relevant academic research and scientific papers
Fluorine-containing butanolides and butenolides. Vinylic fluorine displacement in 4,4-dialkyl-2,3-difluoro-2-buten-4-olides and a novel rearrangement induced by organolithium addition to a carbonyl group
Paleta, Old?ich,Pelter, Andrew,Kebrle, Josef,Duda, Zdeněk,Hajduch, Jan
, p. 3197 - 3207 (2000)
2,3-Difluoro-4,4-dimethyl-2-buten-4-olide (1) and spirocyclic 2,3- difluoro-4,4-(pentane-1,5-diyl)-2-buten-4-olide (2) were modified by vinylic displacement of fluorine with some O- and C-nucleophiles. Sodium and lithium alkoxides, substituted phenoxides and protected glucose alkoxides reacted by 1,4-addition followed by the expulsion of fluoride ion to give 3-substituted derivatives (4-24). Softer Grignard reagents in the form of a copper (I) bromide-dimethyl sulfide complex reacted in the same way as O-nucleophiles to afford 3-alkyl- or 3-aryl derivatives (25-26). Harder organolithium reagents attacked the carbonyl group to give unstable hydroxy compounds that rearranged spontaneously to furan(2H)-3-ones (27-29) in a novel oxygen rearrangement reaction. (C) 2000 Elsevier Science Ltd.
A novel rearrangement induced by the addition of organyllithium reagents to 2,3-difluoro-4,4-dimethylbut-2-enolide
Paleta, Oldrich,Pelter, Andrew,Kebrle, Josef
, p. 9259 - 9262 (1994)
Addition of Q-nucleophiles and Grignard reagents in the presence of copper(I) bromide-dimethyl sulphide to 2,3-difluoro-4,4-dimethylbut-2-enolide proceeds by 1,4-addition and expulsion of a fluoride anion to give 4-substituted butenolides. Organolithium r
