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Journal of Sulfur Chemistry Volume 35, 2014 - Issue 3
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Original Articles

On the thermal Pummerer rearrangement of substituted sulfoxides

Liliana MarzoratiInstitute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, 05508 000São Paulo, SP, BrazilCorrespondence[email protected]
,
Eduardo K.C. YoshikawaInstitute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, 05508 000São Paulo, SP, Brazil
,
Ataualpa A.C. BragaInstitute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, 05508 000São Paulo, SP, Brazil
&
Claudio Di VittaInstitute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes 748, 05508 000São Paulo, SP, Brazil
Pages 248-260 | Received 12 Apr 2013, Accepted 03 Oct 2013, Published online: 07 Nov 2013
 
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Abstract

Sulfoxides bearing thioester and ester groups at the α position under heating at ca. 140°C undergo Pummerer thermal rearrangement. However, for sulfonyl sulfoxide, a complex mixture of products is formed. Plausible mechanism is advanced.

GRAPHICAL ABSTRACT

Acknowledgements

We acknowledge FAPESP, CNPq and CAPES for a scholarship for one of us (EKCY) and for financial support.

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