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Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study
Xiaodong Zou1, Jiaqi Zou1, Lizheng Yang1
1Institute of Chemistry and BioMedical Sciences, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University , Nanjing 210093, China.
The Journal of Organic Chemistry
|April 18, 2017
Abstract:
The rearrangement of sulfamoyl azides under thermal conditions to form a C-C bond while breaking two C-N bonds is reported. Mechanistic study shows that this reaction goes through a Curtius-type rearrangement to form a 1,1-diazene, then which rearranges possibly through both a concerted rearrangement process and a stepwise radical process. This rearrangement could be used in the synthesis of complex biologically active molecules, such as sterols, and piperine derivatives.