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- W2950958598 abstract "The Zn/Barbier reaction of acid-washed zinc or zinc/silver couple with (Z)- or (E)-CF3CFCFI and aromatic aldehydes in DMF stereospecifically gives the (Z)- or (E)-allylic alcohol, CF3CFCFCH(OH)C6H5. Substituted aromatic aldehydes, which contain an electron-withdrawing group, undergo Barbier addition reaction. Substituted aromatic aldehydes, which contain an electron-releasing group, fail to undergo Barbier addition reaction. Aliphatic aldehydes, such as butanal, which contain an α-H, fail to undergo Barbier addition and significant amounts of CF3CFCFH are formed. When the addition reaction is carried out in the presence of 1,4-dinitrobenzene, no reaction is observed. Mechanistically, the Zn/Barbier addition of CF3CFCFI to aromatic aldehydes is best explained by formation of the [CF3CFCF]⊖ anion which adds to the aldehyde and is not adequately explained by formation and addition of an unsolvated zinc reagent, CF3CFCFZnI (unsolvated)." @default.
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- W2950958598 date "2001-10-01" @default.
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- W2950958598 title "The stereospecific Barbier reaction between (Z)- and (E)-1-iodopentafluoropropenes, zinc and aldehydes" @default.
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- W2950958598 doi "https://doi.org/10.1016/s0022-1139(01)00460-2" @default.
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