Abstract
p-Toluenesulfonyl radical can be generated from sodium p-toluenesulfinate in aqueous acetic acid or formic acid. Sulfonyl radical mediating reaction of 5-aryl sbustituted alkenes with sodium p-toluenesulfinate/copper(II) acetate gave p-toluenesulfonylmethyl substituted naphthalene and isoquinoline derivatives. This reaction proceeded much faster in aqueous formic acid than in aqueous acetic acid. The cyclization mode (Ar 2-6 vs Ar 1-5) of the 5-phenyl-1-butly radical is strongly dependent on the geometry of the tether of the radical intermediate.
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