Studies in the pinacol-pinacolone rearrangement Public Deposited

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  • The synthesis of 3,3'-diphenylbenzopinacol was carried out both by means of the Grignard reaction between m-diphenyl magnesium iodide and benzil, and by reduction of m-phenyl benzophenone. The pinacol was rearranged and the products analyzed. The migration aptitude of m-biphenyl was determined to be 1.5. Attempts to prepare 3,3'-diphenyl-4,4'-dimethylbenzopinacol were unsuccessful. 4,4'-dimethoxybenzopinacol was prepared by the grignard reaction but it could not be crystallized; and rearrangement studies were not instigated. Alpha and beta desoxybenzoin pinacols were synthesized. These were very resistant to rearrangement, and ordinary methods gave none of pinacolone. During the synthesis of some of the diphenyl intermediates, the Gomberg-Bachmann synthesis of diaryls was improved upon by substituting potassium carbonate for the strong base. The yield of m-nitroaniline was thus increased by six percent.
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