Abstract
AbstractThe electrolysis of some substituted 3‐arylpropionic acids has been investigated with a view to a possible rearrangement of free radicals formed through discharge of anions.With 3‐phenylisovaleric acid in methanol containing an excess of sodium acetate the main product isolated was t‐amylbenzene, no rearrangement having occurred.3,3,3‐Triphenylpropionic acid in methanol containing sodium ions gave mainly the phenyl ester of 3,3‐diphenyl‐3‐methoxypropionic acid. The analogous tri‐p‐t‐butylphenylpropionic acid yielded the p‐t‐butylphenyl ester of 3,3‐di‐p‐t‐butylphenyl‐3‐methoxypropionic acid. The latter results are interpreted as involving a novel type of rearrangement of acyloxy radicals, an oxygen atom attacking an aromatic ring at its point of attachment to the C‐3 atom:magnified imageIn a discussion on the mechanism of isomerizations occurring in electrolysis, it is suggested that acyloxy radicals may also play a part rather than alkyl radicals only.
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