Sulfur trioxide pyridine complex

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Sulfur trioxide pyridine complex
Sulfur-trioxide-pyridine-complex-2D-skeletal.png Sulfur-trioxide-pyridine-complex-3D-vdW.png
Identifiers
CAS number 26412-87-3 YesY
PubChem 168533
ChemSpider 147422 YesY
Properties
Molecular formula C5H5NSO3
Molar mass 159.16 g/mol
Appearance white solid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Sulfur trioxide pyridine complex is the compound with the formula C5H5NSO3. It is a colourless solid that dissolves in polar organic solvents. It is the adduct formed from the Lewis base pyridine and the Lewis acid sulfur trioxide. The compound is mainly used as a source of sulfur trioxide, for example in the synthesis of sulfate esters from alcohols:[1]

ROH + C5H5NSO3 → [C5H5NH]+[ROSO3]-

It is also an activating electrophile in a Parikh-Doering oxidation.[2]

References[edit]

  1. ^ Thomas T. Tidwell "Sulfur Trioxide–Pyridine" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. doi:10.1002/047084289X.rs139m. Article Online Posting Date: April 15, 2001
  2. ^ Jekishan R. Parikh, William v. E. Doering (1967). "Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide". J. Am. Chem. Soc. 89 (21): 5505–5507. doi:10.1021/ja00997a067. 

Further reading[edit]