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Communication | Special issue | Vol 5, No. 1, 1976, pp.377-399
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0377
Reactions of Halothiophenes with Acetone Enolate and Amide Ions

Joseph F. Bunnett* and Bernhard F. Gloor

*University of California, Santa Cruz, U.S.A.

Abstract

Acetone enolate ion undergoes photostimulated reaction with 2-chloro-, 2-bromo- and 3-bromothiophenes in liquid ammonia, affording mono- and dithienylacetones in fair to good yields. 3-Bromothiophene reacts with the same enolate ion under stimulation by solvated electrons to form mono- and di(3-thienyl)acetones in lower yield accompanied by the corresponding secondary alcohols, except that in the presence of excess KNH2 only debromination to thiophene occurs. Solvated electron-stimulated reactions of 2-chloro- and 2-bromothiophenes with acetone enolate ion give mainly thiophene and little thienylation. Under N2, 3-bromothiophene and KNH2 give 3-aminothiophene in high yield, but not much reaction occurs under an atmosphere of air. These reactions are believed to occur by the SRN1 mechanism. They suggest that substitutions by the SRN1 mechanism may be generally useful in the thiophene series, especially for the preparation of 3-substituted thiophenes.