Abstract
Abstract Dimethyl sulfite reacted with an excess of phenyllithium yielding biphenyl and diphenyl sulfide in good yield. Other dialkyl sulfites also reacted giving identical yields of biphenyl and diphenyl sulfide irrespective of the structure of the aryl groups, indicating that dialkyl sulfites can be used for the reaction with aryllithiums in place of diaryl sulfoxides. The mechanism of the reaction of diaryl sulfoxides with aryllithium is discussed on the basis of the isomer distribution of bitolyls, the effect of additives, and the ratio of the benzyne and sulfonium salt pathways. Sulfurane 1 is formed in an initial stage of the reaction of diaryl sulfoxide with aryllithium followed by its competitive collapse by way of benzyne and sulfonium salt pathways.
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