Sun Haoran, DiMagno Stephen G
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA.
J Am Chem Soc. 2005 Feb 23;127(7):2050-1. doi: 10.1021/ja0440497.
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.
四丁基氟化铵(TBAF)是在低温下通过六氟苯与四丁基氰化铵的亲核芳香取代反应制备的。在该合成过程中,生成的六氰基苯会清除掉痕量水,六氰基苯在碱性条件下很容易与水加成。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除反应是稳定的。已表明添加的羟基溶剂会催化TBAF的分解,并催化与二甲基亚砜的质子交换。简要描述了这种盐的合成用途。