Abstract
Carbonylations of benzyl alcohol and its related compounds are introduced from synthetical and mechanistic viewpoints in conformity with the authors' investigation. Benzyl alcohol is easily carbonylated to form phenylacetic acid in the presence of rhodium chloride and methyl iodide, and the introduction of an electrodonating group into phenyl ring of the alcohol accelerates the reaction. A mechanistic discussion of the reaction is evolved with reference to the oxidative addition of benzylic halides to palladium complexes. In the reaction of benzyl acetate catalyzed by rhodium chloride and methyl iodide phenylacetic acid is unexpectedly formed as the main product, and a mechanistic proposal for the phenonenon is drawn.
