S. Stavber, M. Zupan, A. Poss
Sep 11, 1995
Citations
0
Influential Citations
36
Citations
Journal
Tetrahedron Letters
Abstract
Abstract 1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) ( Accufluor ™ NFTh) is confirmed as a highly effective reagent for introducing a fluorine atom into organic molecules across a phenyl-substituted carbon-carbon double bond. Quantitative and Markovnikov-type regioselective formation of vicinal fluoro-hydroxy, fluoro-methoxy or fluoro-acetoxy adducts was achieved when phenyl-substituted alkenes were treated with a MeCN solution of NFTh In the presence of water, methanol or acetic acid. The stereochemical course of fluoro-methoxylation reactions in the case of cyclic phenyl-substituted alkenes depends strongly on the structure of the alkene.