Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study

Xiaodong Zou, Jiaqi Zou, Lizheng Yang, Guigen Li, Hongjian Lu

Research output: Contribution to journalArticle

4 Scopus citations

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.

Original languageEnglish
Pages (from-to)4677-4688
Number of pages12
JournalJournal of Organic Chemistry
Volume82
Issue number9
DOIs
StatePublished - May 5 2017

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