期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 5, 页码 2740-2755出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00009
关键词
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资金
- Skaggs Institute for Chemical Biology at The Scripps Research Institute
- Georgia Institute of Technology
- National Science Foundation [CHE-1011796]
The in situ preparation and trapping of chlorine azide provided a versatile one-pot method for the azidochlorination of alkenes. Gaseous ClN3 generated from sodium azide, hypochlorite, and acetic acid can be explosive if isolation is attempted. Instead, we generated the reagent in biphasic media in the presence of olefinic compounds dissolved in the organic layer or evenly emulsified throughout the solution in the absence of organic solvent. Under these conditions, ClN3 is created slowly and trapped immediately at the aqueous-organic interface. The resulting safe and reliable procedure provided 1,2-azidochloride derivatives of a variety of substrates, with evidence for both polar and radical mechanisms. Minor impurities characterized in the product mixtures indicated the presence of alternative reaction pathways deriving primarily from radical intermediates.
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