Synthesis of 2-Phenyl-1-(2-thienyl) and 2-Aryl-1-(2-furyl)ethanones by the SRN1 Mechanism. Relative Reactivities of Enolate Ions of ketones.

BAUMGARTNER, M.T.; GALLEGO, M.H.; PIERINI, A. B.

AMER CHEMICAL SOC

Lugar: Washington; Año: 1998 vol. 63 p. 6394 - 6394

e studied the reaction of the enolate ions of 2-acetylthiophene and 2-acetylfuran with different aryl halides to determine their reactivity, the initiation conditions that favor the substitution reaction, and the possibility of increasing their synthetic scope. Photoinitiation and initiation by ferrous ion were carried out. Ferrous ion (usually FeSO4 in liquid ammonia and FeCl2 or FeBr2 in DMSO) can provide an alternative and efficient method to initiate the reaction of carbanions with iodobenzene and other aryl halides. The relative reactivities of the enolate ions of 2-acetylthiophene and 2-acetylfuran with respect to the enolate ions of acetophenone and 2-acetylnaphthalene were determined.