TY - JOUR
T1 - Thermal Rearrangement of Sulfamoyl Azides
T2 - Reactivity and Mechanistic Study
AU - Zou, Xiaodong
AU - Zou, Jiaqi
AU - Yang, Lizheng
AU - Li, Guigen
AU - Lu, Hongjian
N1 - Funding Information:
We are grateful for financial support by National Natural Science Foundation of China (21472085) and Qing Lan Project.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/5/5
Y1 - 2017/5/5
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85019041979&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b00308
DO - 10.1021/acs.joc.7b00308
M3 - Article
C2 - 28414236
AN - SCOPUS:85019041979
SN - 0022-3263
VL - 82
SP - 4677
EP - 4688
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -