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DOI: 10.1055/s-0028-1088019
γ-Chloromagnesio γ-Lactones and δ-Chloromagnesio δ-Lactones: Generation, Properties, and Synthetic Uses
Publication History
Publication Date:
16 March 2009 (online)

Abstract
Treatment of γ- and δ-lactones having a sulfinyl group at the γ- and δ-positions with isopropylmagnesium chloride in THF at -78 ˚C gave γ-chloromagnesio γ-lactones and δ-chloromagnesio δ-lactones, respectively, by the sulfoxide-magnesium exchange reaction in high yields. Comparing the stability of the γ-chloromagnesio γ-lactones with that of the δ-chloromagnesio δ-lactones, the former was found to be much more stable. The reaction of these γ-chloromagnesio γ-lactones and δ-chloromagnesio δ-lactones with electrophiles and the stereochemistry of the reactions are discussed.
Key words
γ-chloromagnesio γ-lactone - δ-chloromagnesio δ-lactone - sulfoxide-magnesium exchange reaction - organomagnesium compound - Grignard reagent
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