Sulfuryl diazide

Sulfuryl diazide
Names
	IUPAC name Sulfuryl diazide
	Other names Sulfuryl azide; Sulfonyl diazide
Identifiers
CAS Number	72250-07-8;
3D model (JSmol)	Interactive image;
ChemSpider	10606313;
PubChem CID	15191028;
	show InChI
	show SMILES
Properties
Chemical formula	N6O2S
Molar mass	148.10 g·mol−1
Melting point	−15 °C (5 °F; 258 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Sulfuryl diazide (sulfuryl azide) is a chemical compound with the molecular formula N₆O₂S. It was first described in the 1920s when its reactions with benzene and p-xylene were studied by Theodor Curtius and .^[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 (SO₂Cl₂) with sodium azide (NaN₃) using acetonitrile as solvent:

SO
2Cl
2 + 2 NaN
3 → SO
2(N
3)
2 + 2 NaCl

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

R¹-NH-R² → R¹-R²

References[]

^ Jump up to: ^a ^b Curtius, Theodor; Schmidt, Friedrich (1922). "Action of sulfuryl azide, N3SO2N3, on p-xylene". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 55B: 1571–1581.CS1 maint: multiple names: authors list (link)
^ Schmidt, Friedrich (1922). "Action of sulfuryl azide on benzene". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 55B: 1581–1583. doi:10.1002/cber.19220550611.
^ Schmidt, K. F. (1925). "Action of sulfuryl azide on benzene". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 58B: 2409–2412. doi:10.1002/cber.19250581027.
^ Jump up to: ^a ^b ^c Xiaoqing Zeng, Helmut Beckers, Eduard Bernhardt, and Helge Willner (2011). "Synthesis and Characterization of Sulfuryl Diazide, O2S(N3)2". Inorg. Chem. 50 (17): 8679–8684. doi:10.1021/ic201294b. PMID 21815651.CS1 maint: multiple names: authors list (link)
^ Xiaodong Zou, Jiaqi Zou, Lizheng Yang, Guigen Li, and Hongjian Lu (2017). "Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study". J. Org. Chem. 82 (9): 4677–4688. doi:10.1021/acs.joc.7b00308. PMID 28414236.CS1 maint: multiple names: authors list (link)
^ Derek Lowe (July 7, 2021). "Carving Out Nitrogens: Pick Your Conditions". In The Pipeline. Science Translational Medicine.
^ Qin, Haitao; Cai, Wangshui; Wang, Shuang; Guo, Ting; Li, Guigen; Lu, Hongjian (2021). "N‐Atom Deletion in Nitrogen Heterocycles". Angewandte Chemie International Edition. doi:10.1002/anie.202107356. PMID 34227207.

[Curtius-1] Jump up to: ^a ^b Curtius, Theodor; Schmidt, Friedrich (1922). "Action of sulfuryl azide, N3SO2N3, on p-xylene". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 55B: 1571–1581.CS1 maint: multiple names: authors list (link)

[2] Schmidt, Friedrich (1922). "Action of sulfuryl azide on benzene". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 55B: 1581–1583. doi:10.1002/cber.19220550611.

[3] Schmidt, K. F. (1925). "Action of sulfuryl azide on benzene". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 58B: 2409–2412. doi:10.1002/cber.19250581027.

[Zeng-4] Jump up to: ^a ^b ^c Xiaoqing Zeng, Helmut Beckers, Eduard Bernhardt, and Helge Willner (2011). "Synthesis and Characterization of Sulfuryl Diazide, O2S(N3)2". Inorg. Chem. 50 (17): 8679–8684. doi:10.1021/ic201294b. PMID 21815651.CS1 maint: multiple names: authors list (link)

[5] Xiaodong Zou, Jiaqi Zou, Lizheng Yang, Guigen Li, and Hongjian Lu (2017). "Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study". J. Org. Chem. 82 (9): 4677–4688. doi:10.1021/acs.joc.7b00308. PMID 28414236.CS1 maint: multiple names: authors list (link)

[6] Derek Lowe (July 7, 2021). "Carving Out Nitrogens: Pick Your Conditions". In The Pipeline. Science Translational Medicine.

[7] Qin, Haitao; Cai, Wangshui; Wang, Shuang; Guo, Ting; Li, Guigen; Lu, Hongjian (2021). "N‐Atom Deletion in Nitrogen Heterocycles". Angewandte Chemie International Edition. doi:10.1002/anie.202107356. PMID 34227207.

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[2]

[3]

[4]

[5]

[6]

[7]

Sulfuryl diazide

See also[]

References[]