Reactions of TaF5 with activated arenes. Synthesis of [4-(OH)-3-(OCH3)C6H3CH(OH)][4-(OH)-3-(OCH3)C6H3CHO][TaF6], a rare example of protonated aldehyde

The rare example of protonated aldehyde salt [4-(OH)-3-(OCH3)C6H3CH(OH)][4-(OH)-3-(OCH3)C6H3CHO][TaF6], 1, was isolated in the solid state by the reaction of 4-hydroxy-3-methoxybenzaldehyde (vanillin) with TaF5 in dichloromethane. The product 1 was characterized by X-ray diffraction and IR spectroscopy. The 1:1 reaction of TaF5 with N,N-dimethylaniline in CH2Cl2 cleanly afforded [TaF4(NMe2C6H5)2][TaF6], 2, which was identified by NMR spectroscopy. Attempts of crystallization of 2 resulted in the isolation of the ammonium salt [NHMe2C6H5][TaF6], 3.

The protonated aldehyde salt [4-(OH)-3-(OCH3)C6H3CH(OH)][4-(OH)-3-(OCH3)C6H3CHO][TaF6] was isolated in the solid state by the reaction of vanillin with TaF5 in dichloromethane and structurally characterized.Figure optionsDownload as PowerPoint slide