Conversion of phenols into selenophenols: seleno Newman-Kwart rearrangement

Angew Chem Int Ed Engl. 2013 Nov 18;52(47):12346-9. doi: 10.1002/anie.201303773. Epub 2013 Sep 17.

Abstract

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. The aryl selenols (isolated as the diselenides) can be prepared by hydrolysis of the Se-aryl selenocarbamates.

Keywords: X-ray crystallography; density functional calculations; kinetics; rearrangement; selenium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemical synthesis
  • Benzene Derivatives / chemistry*
  • Carbamates / chemistry
  • Crystallography, X-Ray
  • Kinetics
  • Molecular Conformation
  • Organoselenium Compounds / chemical synthesis
  • Organoselenium Compounds / chemistry*
  • Oxidation-Reduction
  • Phenols / chemistry*
  • Thermodynamics

Substances

  • Benzene Derivatives
  • Carbamates
  • Organoselenium Compounds
  • Phenols
  • benzeneselenol