RESUMO
F5S-C≡C-CF3 can be easily prepared in high yields in two steps from 3,3,3-trifluoropropyne. It is a powerful, versatile dienophile in Diels-Alder reactions. Reactions at room temperature provide the corresponding products in up to quantitative yields allowing the introduction of the pentafluorosulfanyl group and trifluoromethyl group at the 1,2 position.
RESUMO
Acetylenephosphonates carrying the XCF(2) group have been studied in a base-mediated heterocyclization reaction with selected 2-amino-3-formylchromones to give 2-difluoromethyl azaxanth-3-ylphosphonates. The presence of the fluorinated substituent determined the regioselectivity as well as the reactivity of this process.
Assuntos
Alcinos/química , Fluorocarbonos/química , Organofosfonatos/química , Piridinas/síntese química , Xantonas/síntese química , Ciclização , Estrutura Molecular , Piridinas/química , Estereoisomerismo , Xantonas/químicaRESUMO
An efficient synthesis of 2-perfluoroalkyl 4H-chromen-3-ylphosphonates 4a-i (R(F) = CF(3)) and 5a-i (R(F) = C(2)F(5)) has been accomplished via regioselective cycloaddition of 2-hydroxybenzaldehydes to diethyl 3,3,3-trifluoropropyn-1-yl- and diethyl 3,3,4,4,4-pentafluorobutyn-1-ylphosphonate, using trialkyl amines or phosphines as mediators. 2H-Chromen-3-ylphosphonates 6a-i were regioselectively obtained in the presence of triphenylphosphine. A convenient method for the isomerization of 4H-chromen-3-ylphosphonates into 2H-chromen-3-ylphosphonates 6a-i (R(F) = CF(3)) and 7a-i (R(F) = C(2)F(5)) was established.