What is it about?
Butane-1,4-diol was fluoroalkylated by its photoaddition reactions with hexafluoropropene and perfluoro (propyl vinyl) ether under atmospheric pressure, by which monofluoroalkylated and bis-fluoroalkylated products were obtained. 1,3-Diols were completely unreactive under the conditions. 2,2,2-Trifluoroethanol, tert.butyl alcohol and methyl tert.butyl ether appeared to be inert solvents for the additions while acetonitrile quenched the reactions. The reactivity of perfluoro vinyl ethers was studied (tested) in their photoaddition reactions with alkanols that were less regioselective (up to 7% rel.of regioisomer) in comparison with hexafluoropropene. Surprisingly, photo-supported base-induced nucleophilic monoand bis-addition of butane-1,4-diol onto hexafluoropropene was observed in acetonitrile.
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Why is it important?
Butane-1,4-diol was fluoroalkylated by its photoaddition reactions with hexafluoropropene and perfluoro (propyl vinyl) ether under atmospheric pressure, by which monofluoroalkylated and bis-fluoroalkylated products were obtained. 1,3-Diols were completely unreactive under the conditions. 2,2,2-Trifluoroethanol, tert.butyl alcohol and methyl tert.butyl ether appeared to be inert solvents for the additions while acetonitrile quenched the reactions. The reactivity of perfluoro vinyl ethers was studied (tested) in their photoaddition reactions with alkanols that were less regioselective (up to 7% rel.of regioisomer) in comparison with hexafluoropropene. Surprisingly, photo-supported base-induced nucleophilic monoand bis-addition of butane-1,4-diol onto hexafluoropropene was observed in acetonitrile.
Perspectives
Butane-1,4-diol was fluoroalkylated by its photoaddition reactions with hexafluoropropene and perfluoro (propyl vinyl) ether under atmospheric pressure, by which monofluoroalkylated and bis-fluoroalkylated products were obtained. 1,3-Diols were completely unreactive under the conditions. 2,2,2-Trifluoroethanol, tert.butyl alcohol and methyl tert.butyl ether appeared to be inert solvents for the additions while acetonitrile quenched the reactions. The reactivity of perfluoro vinyl ethers was studied (tested) in their photoaddition reactions with alkanols that were less regioselective (up to 7% rel.of regioisomer) in comparison with hexafluoropropene. Surprisingly, photo-supported base-induced nucleophilic monoand bis-addition of butane-1,4-diol onto hexafluoropropene was observed in acetonitrile.
Dr Vladimír Církva
Institute of Chemical Process Fundamentals
Read the Original
This page is a summary of: Radical additions to fluoroolefins. Photochemical fluoroalkylation of alkanols and alkane diols with perfluoro vinyl ethers; photo-supported O-alkylation of butane-1,4-diol with hexafluoropropene, Journal of Fluorine Chemistry, October 1996, Elsevier,
DOI: 10.1016/s0022-1139(96)03514-2.
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