Superbase-Assisted Addition of Phosphine to 1-Methoxy-4-vinylbenzene: Toward a Rare Family of Organic Phosphines
摘要:
Phosphine reacts with 1-methoxy-4-vinylbenzene in the superbase suspension KOH-dimethylsulfoxide (70-100 degrees C, atmospheric pressure) to form regiospecifically anti-Markovnikov adducts, bis[2-(4-methoxyphenyl)ethyl]phosphine (1) and tris[2( 4-methoxyphenyl) ethyl] phosphine (2), representatives of rare arylalkylphosphines. The conditions for the selective preparation of phosphines 1 or 2 in 67% and 80% yields, respectively, have been elaborated. The phosphines have been oxidized with aqueous solution of H2O2, elemental sulfur, or selenium to afford the corresponding phosphine chalcogenides in good yields (95-99%).