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Towards New Imidazole-2-Thione-Based Organocatalysts; Sulfur Transfer Vs. Deoxygenation in the Reaction of Imidazole N-Oxides and Cycloaliphatic Thioketones

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Sulfuration or deoxygenation? Competitive transformations of the title imidazole N-oxides into respective masked thiourea analogs or into the parent heterocycle in the reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione are presented. The influence of an electron-withdrawing substituents in combination with the steric hindrance of neighboring groups onto reaction outcome is discussed.
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Keywords: deoxygenation; imidazole N-oxides; sulfur transfer; trans-1,2-Diaminocyclohexane

Document Type: Research Article

Affiliations: 1: Department of Organic and Applied Chemistry, University of Łódź, Łódź, Poland 2: Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse, Zürich, Switzerland

Publication date: 01 April 2013

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