Anhydrous tetrabutylammonium fluoride
Anhydrous tetrabutylammonium fluoride
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DOI：
10.1021/ja0440497
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发表时间：
2005-02-23
影响因子：
15
通讯作者：
DiMagno, SG
中科院分区：
文献类型：
--
作者：
Sun, HR;DiMagno, SG
以六氟苯为原料，采用氰化四丁基铵在低温下亲核芳烃取代制得四丁基氟化铵（TBAF）。在这个合成过程中，外来的水被生成的六正苯基清除，它在基本条件下很容易加水。与预期相反，在无水条件下，TBAF在极性非质子溶剂中对霍夫曼消去是稳定的。添加羟基溶剂可以催化TBAF的分解和催化与DMSO的质子交换。简述了该盐的合成用途。
Tetrabutylammonium fluoride (TBAF) is prepared at low temperature by nucleophilic aromatic substitution of hexafluorobenzene with tetrabutylammonium cyanide. Adventitious water is scavenged during this synthesis by the generated hexacyanobenzene, which readily adds water under basic conditions. Contrary to expectations, TBAF is stable to Hofmann elimination in polar aprotic solvents under anhydrous conditions. Added hydroxylic solvents are shown to catalyze the decomposition of TBAF and to catalyze proton exchange with DMSO. The synthetic utility of this salt is described briefly.