Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study

Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study
Xiaodong Zou, Guigen Li, Jiaqi Zou, Lizheng Yang, Hongjian Lu
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00308

DOI: 10.1021/acs.joc.7b00308

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