Vicinal bromofluoroalkanes: their regioselective formation and their conversion to fluoro olefins
Reaction of alkenes with N-bromosuccinimide and Et3N.3HF produces vic-bromofluoroalkanes in high yields. As long as the addn. to the C:C bond is sterically unhindered, Br and F get attached with very high regioselectivity, the latter occupying the more substituted, carbocation-stabilizing position. 2-Fluoro-1-alkenes give 1-bromo-2,2-difluoroalkanes. The Br may be removed by base-promoted dehydrofluorination to afford fluoro olefins, or by redn. with Bu3SnH, leading to mono- or difluoroalkanes. [on SciFinder (R)]
1990
46
12
4255
4260
CAN 114:5761
23-3
Aliphatic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
100-42-5; 106-24-1 (Geraniol); 107-39-1 (2,4,4-Trimethyl-1-pentene); 558-37-2 (3,3-Dimethyl-1-butene); 872-05-9 (1-Decene); 130876-17-4 Role: RCT (Reactant), RACT (Reactant or reagent) (bromofluorination of); 7206-17-9; 7206-29-3; 14850-23-8 Role: RCT (Reactant), RACT (Reactant or reagent) (bromofluorination of, regiochem. of); 10035-10-6 Role: RCT (Reactant), RACT (Reactant or reagent) (dehydrobromination, of bromofluoroalkanes with potassium tert-butoxide); 696-31-1P (1-Fluoro-1-phenylethylene) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and bromofluorination of); 1786-34-1P (1-Bromo-2-fluorodecane); 1786-36-3P; 130876-09-4P; 130876-10-7P; 130876-11-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and elimination reaction of, with potassium tert-butoxide); 108661-89-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with tributyltin hydride); 657-35-2P (1,1-Difluoro-1-phenylethane); 101166-45-4P; 119105-46-3P; 119105-47-4P; 129973-52-0P; 130876-12-9P; 130876-13-0P; 130876-14-1P; 130876-15-2P; 130876-16-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
REVIEWED
EPFL