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Paper | Regular issue | Vol 34, No. 5, 1992, pp.1039-1046
Published online, 1st January, 1970
DOI: 10.3987/COM-92-5994
Study of the Reaction of Several Ketone Enolates with 3-Iodobenzo[b]thiophene under Thermally Initiated SRN1 Reaction Conditions

Montserrat Prats,* Carmen Gálvez, and Lluís Beltran

*Departament de Química Orgànica, Universitat de Barcelona, Martí i Franquès, 1-11, 08028 Barcelona, Spain

Abstract

The reaction of 3-iodobenzo[b]thiophene (1) with the potassium enolates of cyclohexanone (2a), acetone (2b), and acetophenone (2c) in DMSO for 1 h at room temperature in the dark, gave the desired α-hetaryl ketones (3a-c) in low yield. The thermally activated SRN1 reaction with the ion enolate (2a) was studied in more detail and it was found that the radical chain SRN1 mechanism could compete with one of ionic character.