Tandem Nucleophilic Additions of Aryloxides

Article abstract of DOI:10.1021/jo00001a031

Hydroquinone disodium salt added sequentially to tetrafluoroethylene and carbon dioxide to yield a symmetrical dicarboxylic acid, which was transformed into the corresponding dimethyl ester, diol, diamide, and diamine.Chlorotrifluoroethylene in analogous reactions gave the corresponding diester and diol in excellent yield.When this kind of transformation was attempted on phloroglucinol, the Kolbe-Schmitt carboxylation reaction intervened.Despite serious competition from addition/elimination processes under typical reaction conditions, the tandem addition of phenoxide ion to hexafluoropropene and carbon dioxide was carried out successfully at lower temperatures and higher carbon dioxide pressures.