کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5216935 | 1383280 | 2013 | 7 صفحه PDF | دانلود رایگان |
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 α-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.
Journal: Tetrahedron - Volume 69, Issue 36, 9 September 2013, Pages 7840-7846