Exploring the reactivity of 1,5-disubstituted sulfonyl-triazoles: Thermolysis and Rh(II)-catalyzed synthesis of a-sulfonyl nitriles

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Mitchell Croatt, Assistant Professor (Creator)
Maria Elena Meza-Avina, Research Scientist (Creator)
The University of North Carolina at Greensboro (UNCG )
Web Site: http://library.uncg.edu/

Abstract: The reactivity of a series of 1,5-disubstituted sulfonyl-triazoles was explored using either thermolytic or metal-catalyzed conditions. Both the thermolysis and the Rh(II)-catalyzed reactions led to the synthesis of a-sulfonyl-nitriles, which presumably occurred through a carbene or carbenoid mechanism. The reactivity of the carbenes and carbenoids resulting from the loss of dinitrogen from the 1,5-disubstituted sulfonyl-triazoles were different from those of the previously explored 1,4-disubstituted sulfonyl-triazoles. It was observed by NMR that the Rh(II)-catalyst coordinates strongly but reversibly with the 1,5-disubstituted sulfonyl-triazoles. Other catalysts, including both Brønsted and Lewis acids, were found to catalyze this transformation, although less efficiently compared to neat thermolysis or Rh(II)-catalyzed conditions. These data illustrate both the unique nature of 1,5-disubstituted sulfonyl-triazoles and potential future avenues for their utilization.

Additional Information

Language: English
Date: 2013
Triazoles, Thermolysis, Rhodium, Nitriles, Carbenes, organic chemistry

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