RESUMEN
Activation of the relatively inactive polypyridine backbone with strong electrophilic fluorine, originating from acetyl hypofluorite (AcOF) enables attack of the acetoxy moiety at the α position to the heteroatom. Derivatives of bipyridine, phenanthroline and terpyridine systems have been acetoxylated or oxygenated within a few minutes usually in very good yields.
RESUMEN
A novel synthesis of different aromatic and heteroaromatic difluorodioxole derivatives has been developed. The starting materials were catechols, which, after treatment with thiophosgene, formed at 0 °C the respective thiodioxoles. The latter were reacted for a short time with commercially available bromine trifluoride, producing potentially biologically important difluoroaryldioxoles in moderate to high yields.
Asunto(s)
Compuestos de Bromina/química , Compuestos de Flúor/síntesis química , Oxígeno/química , Compuestos de Flúor/química , Estructura MolecularRESUMEN
A synthesis of a wide range of different aliphatic, aromatic, and heterocyclic N-(trifluoromethyl)amides along with aromatic N-(difluoromethylene)-N-(trifluoromethyl)amine derivatives has been developed. The starting materials are the easily available isothiocyanates, and the fluorinating reagent is the commercially available bromine trifluoride. The reaction is performed under mild conditions, and the fluorinated amides and amines are produced in moderate to high yields.
Asunto(s)
Amidas/síntesis química , Compuestos de Bromina/química , Compuestos de Flúor/química , Amidas/química , Estructura MolecularRESUMEN
A general preparation for aromatic and aliphatic, cyclic as well as linear, symmetric and asymmetric difluoromethylenedioxy derivatives is described. The alcohols were reacted with thiophosgene to give thiocarbonates, which in turn were reacted with BrF3. The fluorination step is complete in seconds with moderate to high yields under mild conditions.
Asunto(s)
Compuestos de Bromina/química , Compuestos de Flúor/química , Hidrocarburos Acíclicos/síntesis química , Hidrocarburos Cíclicos/síntesis química , Hidrocarburos Fluorados/síntesis química , Alcoholes/química , Carbonatos/química , Éter/química , Modelos Químicos , Fosgeno/análogos & derivados , Fosgeno/química , Estereoisomerismo , Compuestos de Sulfhidrilo/químicaRESUMEN
This work demonstrates the unique features of the never used before Pyâ¢BrF(3) complex in the field of aromatic organic fluorinations. The main disadvantage of the noncomplexed BrF(3) is the fact that usually, in addition to the desired fluorination, a parallel electrophilic aromatic bromination takes place as well. Use of the Pyâ¢BrF(3) complex reduces this electrophilic bromination, which is observed with most reagents based on fluorine and bromine [BrF].