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Effect of Counter Anions on the Lewis Acidity of Lithium Ion in Trityl Cation Formation

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Abstract A trityl cation was generated from the reactions of trityl chloride and trityl alcohol with alkaline salt catalysts in weakly coordinating dichloromethane. The generated trityl cation was monitored by... UV spectra. In the case of trityl chloride, the catalytic activities were not so different among alkaline salt catalysts such as H_3OTFPB, LiTFPB, NaTPFPB, NaTFPB, and others. These results indicated that anhydrous Li and Na salts have comparable activities to H_3OTFPB in the formation of trityl cation from trityl chloride. On the other hand, the amount of trityl cation generated from trityl alcohol by LiTFPB is one fourteenth as much as the amount generated by H_3OTFPB. This is due to the stronger affinity of Li^+ to alcohols than to chlorides. Furthermore, hydrated alkaline salts have a lower catalytic activity than anhydrous ones because the water decreases the Lewis acidity of Li^+.show more

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Created Date 2009.04.22
Modified Date 2020.12.15

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