Volume 31, Issue 32
Preparative Organic Chemistry
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ChemInform Abstract: Surface-Mediated Reactions. Part 8. Oxidation of Sulfides and Sulfoxides with tert-Butyl Hydroperoxide and OXONE.

Paul J. Kropp

Paul J. Kropp

Dep. Chem., Univ. N. C., Chapel Hill, NC 27599, USA

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Gary W. Breton

Gary W. Breton

Dep. Chem., Univ. N. C., Chapel Hill, NC 27599, USA

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John D. Fields

John D. Fields

Dep. Chem., Univ. N. C., Chapel Hill, NC 27599, USA

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Jesse C. Tung

Jesse C. Tung

Dep. Chem., Univ. N. C., Chapel Hill, NC 27599, USA

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Brian R. Loomis

Brian R. Loomis

Dep. Chem., Univ. N. C., Chapel Hill, NC 27599, USA

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First published: 03 June 2010

Abstract

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ChemInform Abstract

Oxidation of sulfides to sulfoxides occurs readily with tBuOOH over SiO2 or with Oxone over either SiO2 or Al2O3, whereas the greatest selectivity is obtained by Oxone over Al2O3. Oxidation of sulfoxides to sulfones occurs with both tBuOOH or Oxone over either SiO2 or Al2O3. Selective oxidation of sulfides to either sulfoxide or sulfone is achieved by simple stoichiometric control (1 or 2 equiv. tBuOOH).

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