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Valiulin RA, Mamidyala S, Finn MG. Taming chlorine azide: access to 1,2-azidochlorides from alkenes. J Org Chem. 2015;80(5):2740-55doi: 10.1021/acs.joc.5b00009.
Valiulin, R. A., Mamidyala, S., & Finn, M. G. (2015). Taming chlorine azide: access to 1,2-azidochlorides from alkenes. The Journal of organic chemistry, 80(5), 2740-55. https://doi.org/10.1021/acs.joc.5b00009
Valiulin, Roman A, et al. "Taming chlorine azide: access to 1,2-azidochlorides from alkenes." The Journal of organic chemistry vol. 80,5 (2015): 2740-55. doi: https://doi.org/10.1021/acs.joc.5b00009
Valiulin RA, Mamidyala S, Finn MG. Taming chlorine azide: access to 1,2-azidochlorides from alkenes. J Org Chem. 2015 Mar 06;80(5):2740-55. doi: 10.1021/acs.joc.5b00009. Epub 2015 Feb 26. PMID: 25719396.
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J Org Chem. 2015 Mar 06;80(5):2740-55. doi: 10.1021/acs.joc.5b00009. Epub 2015 Feb 26.

Taming chlorine azide: access to 1,2-azidochlorides from alkenes.

The Journal of organic chemistry

Roman A Valiulin, Sreeman Mamidyala, M G Finn

Affiliations

  1. School of Chemistry and Biochemistry, Georgia Institute of Technology , 901 Atlantic Drive, Atlanta, Georgia 30332-0400, United States.

PMID: 25719396 DOI: 10.1021/acs.joc.5b00009

Abstract

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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