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An Electrocatalytic Newman-Kwart-type Rearrangement

Timo Broese, Arend F. Roesel, Adrian Prudlik, Robert Francke*

*Institute of Chemistry, Rostock University, Albert-Einstein-Str. 3a, 18059 Rostock, Germany, Email:

T. Broese, A. F. Roesel, A. Prudlik, R. Francke, Org. Lett., 2018, 20, 7483-7487.

DOI: 10.1021/acs.orglett.8b03257

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An electrochemical approach toward rearrangement of O-aryl thiocarbamates to S-aryl thiocarbamates at room temperature requires only catalytic amounts of electric charge. The electrolysis can be carried out with the simple equipment under galvanostatic conditions in an undivided cell. In a microflow reactor, almost quantitative yields can be achieved without using a supporting electrolyte.

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proposed mechanism

Key Words

Newman-Kwart Rearrangement, Electrochemistry, Thiophenols

ID: J54-Y2018