Sulfuryl diazide explained

Sulfuryl diazide or sulfuryl azide is a chemical compound with the molecular formula . It was first described in the 1920s when its reactions with benzene and p-xylene were studied by Theodor Curtius and Karl Friedrich Schmidt.[1] [2] [3] The compound is reported as having "exceedingly explosive, unpredictable properties" and "in many cases very violent explosions occurred without any apparent reason".[1]

It was not until 2011 that sulfuryl diazide was isolated in a pure enough state to be fully characterized.[4] It was characterized by infrared and Raman spectroscopy; its structure in the solid state was determined by x-ray crystallography.[4] Its melting point is -15 °C.[4] It was prepared by the reaction of sulfuryl chloride with sodium azide using acetonitrile as solvent:

Sulfuryl diazide has been used as a reagent to perform reactions that remove nitrogen from heterocyclic compounds:[5] [6] [7]

See also

Notes and References

  1. Action of sulfuryl azide, N3SO2N3, on p-xylene . Curtius, Theodor
    Schmidt, Friedrich
    . Berichte der Deutschen Chemischen Gesellschaft B . 1922 . 55B . 1571–1581 .
  2. Action of sulfuryl azide on benzene . Schmidt, Friedrich . Berichte der Deutschen Chemischen Gesellschaft B . 1922 . 55B . 1581–1583 . 10.1002/cber.19220550611 .
  3. Action of sulfuryl azide on benzene . Schmidt, K. F. . Berichte der Deutschen Chemischen Gesellschaft B . 1925 . 58B . 2409–2412 . 10.1002/cber.19250581027 .
  4. Synthesis and Characterization of Sulfuryl Diazide, O2S(N3)2 . Xiaoqing Zeng, Helmut Beckers, Eduard Bernhardt, and Helge Willner . Inorg. Chem. . 2011 . 50 . 17 . 8679–8684 . 10.1021/ic201294b . 21815651 .
  5. Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study . Xiaodong Zou, Jiaqi Zou, Lizheng Yang, Guigen Li, and Hongjian Lu . J. Org. Chem. . 2017 . 82 . 9 . 4677–4688 . 10.1021/acs.joc.7b00308 . 28414236 .
  6. Web site: Carving Out Nitrogens: Pick Your Conditions . . July 7, 2021 . In The Pipeline . . June 5, 2023 . live . https://ghostarchive.org/archive/oT8vo . June 5, 2023.
  7. 10.1002/anie.202107356 . N-Atom Deletion in Nitrogen Heterocycles . 2021 . Qin . Haitao . Cai . Wangshui . Wang . Shuang . Guo . Ting . Li . Guigen . Lu . Hongjian . Angewandte Chemie International Edition . 60 . 38 . 20678–20683 . 34227207 . 235746021 .

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