Volume 27, Issue 11
Preparative Organic Chemistry
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ChemInform Abstract: A Theoretical and Experimental Investigation of the Electrophilic Oxidation of Thioethers and Sulfoxides by Peroxides.

M. BONCHIO

M. BONCHIO

Dip. Chim. Org., Univ. Padova, I-35131 Padova, Italy

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S. CAMPESTRINI

S. CAMPESTRINI

Dip. Chim. Org., Univ. Padova, I-35131 Padova, Italy

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V. CONTE

V. CONTE

Dip. Chim. Org., Univ. Padova, I-35131 Padova, Italy

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F. DI FURIA

F. DI FURIA

Dip. Chim. Org., Univ. Padova, I-35131 Padova, Italy

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S. MORO

S. MORO

Dip. Chim. Org., Univ. Padova, I-35131 Padova, Italy

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First published: March 12, 1996

Abstract

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ChemInform Abstract

It is found that the reactivity of sulfoxides like (II) in oxidation is less affected by structural effects than that of thioethers such as (I). The reactivity of thioethers depends almost exclusively on the charge of sulfur atom, whereas in the case of sulfoxides interaction between the HOMO of substrate and the LUMO of oxidant is the relevant factor.

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