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

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  • トリチルカチオン生成反応に及ぼすリチウムイオンの求電子反応性の定量化
  • トリチル カチオン セイセイ ハンノウ ニ オヨボス リチウム イオン ノ キュウデンシ ハンノウセイ ノ テイリョウカ

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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^+.

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