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Conversion of Phenols into Selenophenols: Seleno Newman–Kwart Rearrangement

Authors


  • We acknowledge financial support from the Danish Research council (FNU) for a Steno Fellowship (M.P.) and the Lundbeck Foundation for a Young Group Leader Fellowship (M.P.). We thank Dr. S. R. Beeren for valuable discussions.

Abstract

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A ‘Se'lling point: The first thermally induced OAr→SeAr migration reaction is reported, and it can be used to prepare aryl selenols in three steps from the corresponding phenols. O-aryl selenocarbamates rearrange to Se-aryl carbamates via a four-membered transition state (see scheme). The aryl selenols (isolated as the diselenides) can be prepared by hydrolysis of the Se-aryl selenocarbamates.

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