N-Sulfinylaniline

N-Sulfinylaniline
Names
Other names
N-thionylaniline, phenyliminooxosulfurane
Identifiers
1122-83-4
Properties
C6H5NSO
Molar mass 139.18
Appearance yellowish oil
Density 1.236 g/mL
Boiling point 88–95 °C (17–20 mm.)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

N-Sulfinylaniline is the organosulfur compound with the formula C6H5NSO. It is a straw-colored liquid that is classified as a heterocumulene, being closely related to sulfur dioxide. as well as sulfur diimide, it is a dienophile[1] and a ligand in organometallic chemistry.[2]

Synthesis and structure

It is prepared by treating aniline with thionyl chloride.[3]

3 PhNH2 + SOCl2 → PhNSO + 2 [PhNH3]Cl

The structure of the related trityl derivative has been verified crystallographically.[4]

References

  1. Kresze, G.; Wucherpfennig, W., "Organic synthesis with imides of sulfur dioxide", Angew. Chem. Int. Ed. Engl. 1967, volume 6, 149-167. doi:10.1002/anie.196701491
  2. Hill, A. F., "Organotransition metallic chemistry of sulfur dioxide analogs", Adv. Organomet. Chem. 1994, 36, 159-227.
  3. S. Rajagopalan, B. G. Advani, and C. N. Talaty "Diphenylcarbodiimide" Org. Synth. 1969, volume 49, p. 70. doi:10.15227/orgsyn.049.0070.
  4. Christe, K. O.; Gerken, M.; Haiges, R.; Schneider, S.; Schroer, T.; Tham, F. S.; Vij, A., "Tritylsulfinylamine: a new member in the family of sulfinylamines", Solid State Sciences 2002, volume 4, pp. 1529-1534. doi:10.1016/S1293-2558(02)00049-3.
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