A study of twelve examples of the Schonberg rearrangement of diaryl thioncarbonates to diaryl thiolcarbonates has shown that the reaction is favored by electron-withdrawing groups in the 07th and para positions. It is suggested that the reaction involves a cyclic transition state, with a nucleophilic attack of the thion sulfur on the aromatic nucleus. The similarity of this rearrangement to the Smiles, Chapman and Stevens rearrangements, and to reactions involving a shift from oxygen to sulfur, is discussed.The rearrangement of diaryl thioncarbonates I to diaryl thiolcarbonates I1 which was discovered by Schonberg2 offers a way of converting phenols to S 0 II A /I ArOCOAr + ArOCSAr I I1 t iH20, OH-2ArOH + S = CC12 ArOH + ArSH

No abstract