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

Abstract

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.

GRAPHICAL ABSTRACT

Keywords:

• trans-1,2-Diaminocyclohexane
• imidazole N-oxides
• sulfur transfer
• deoxygenation

ACKNOWLEDGMENTS

Financial support by the Rector of the University of Łódź (Grant no. 505/712/R) and technical assistance in the laboratory work by Mrs Małgorzata Celeda, University of Łódź, are gratefully acknowledged.