154145-31-0Relevant academic research and scientific papers
Triphenylphosphanodefluorination of fluoranil and its derivatives
Zhivetyeva,Selivanova,Goryunov,Bagryanskaya, I.Yu.,Shteingarts
, p. 21 - 32 (2015)
The reaction of 2-X-trifluoro-1,4-benzoquinones (X = F, Cl, Me, OMe) with triphenylphosphane in various solvents (C6H6, Et2O, THF, dioxane, MeOH, aq. dioxane and Me2SO) has been investigated. It was shown that: (1) the quinones react with PPh3 at an oxygen atom and at a carbon atom with formation of products of reduction and of triphenylphosphanodefluorination, accordingly; (2) the use of more polar solvents, such as MeOH, aq. dioxane and Me2SO, leads to an increase in products of phosphanodefluorination; (3) triphenylphosphanodefluorination of 2-X-trifluoro-1,4-benzoquinones (X = Cl, Me, OMe) takes place at positions 5 and 6 to X in ratios depending on the nature of the substituent X. Possible reasons for obtained results are discussed in detail. The entry of solvent molecule into products of phosphanodefluorination of fluoranil was observed in MeOH. The triphenyl(3,4,6,6-tetrafluoro-2-oxido-5-oxocyclohexa-1,3-dien-1-yl)phosphanium and its analogs serves as starting material for a new type of nitrogen-containing phosphorus compounds. The structures of isolated betaines were proved by the XRD and the 19F, 31P{1H} and 13C{1H} NMR data.
