M. Gingras
Dec 9, 1991
Citations
0
Influential Citations
57
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Tetrabutylammonium difluorotriphenylstannate ( 1 ) is the first hypervalent complex of tin acting as a fluorinating agent. In contrast to TBAF and TASF, this crystalline complex is relatively stable up to 210°C and is not hygroscopic or hydrated. Enolsilylether alkylations with alkyl bromides proceeded in good to quantitative yields in the presence of ( 1 ), which was kept for years unprotected from moisture. Relative rate studies indicated that nucleophilic fluorination of benzyl bromide proceeded 18 times faster than with dried cesium fluoride in refluxing CH 3 CN.