139301-01-2Relevant academic research and scientific papers
TETRABUTYLAMMONIUM DIHYDROGENTRIFLUORIDE: AN EFFECTIVE SOURCE OF FLUORIDE ION FOR HALOFLUORINATION OF ALKENES
Albanese, Domenico,Landini, Dario,Penso, Michele,Pratelli, Marco
, p. 537 - 541 (2007/10/02)
Vicinal halofluorides have been prepared from the corresponding alkenes by reaction with a stoichiometric amount of Bu4N+H2F3- as a source of fluoride anion and an excess of an N-halosuccinimide (NXS).The reaction products are obtained in good yields, with a prevalent Markownikoff regiochemistry.Olefins containing hydroxy, epoxy, acetoxy and alkoxy groups do not undergo side reactions under these reaction conditions.
SYNTHESIS OF β-FLUOROAZIDES : A ROUTE TO PRIMARY β-FLUORO AMINES
Benaissa, T.,Hamman, S.,Beguin, C.G.
, p. 163 - 174 (2007/10/02)
Two ways for the synthesis of β-fluoroazides are presented.The first one uses 1,2,2-trifluoro-2-chloro triethylamine (FAR) as a fluorinating reagent on the corresponding azidoalcohols.It is a smooth reaction at room temperature, but is not stereospecific ; it works well for phenyl substituted or primary α-carbon β-fluoroazides.The second route is the substitution of the azide group for bromine on an appropriate fluorobromide in phase transfer conditions.It is stereospecific (except for one case).It works well to give pure diastereoisomers of β-fluoroazides with pseudo primary (with deuterium) or secondary α-carbon atoms.
