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Sulfur trioxide pyridine complex

Summary

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]

Sulfur trioxide pyridine complex
Identifiers
  • 26412-87-3 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 147422 checkY
ECHA InfoCard 100.043.334 Edit this at Wikidata
  • 168533
  • DTXSID50885349 Edit this at Wikidata
  • InChI=1S/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H; checkY
    Key: UDYFLDICVHJSOY-UHFFFAOYSA-N checkY
  • InChI=1/C5H5N.O3S/c1-2-4-6-5-3-1;1-4(2)3/h1-5H;
    Key: UDYFLDICVHJSOY-UHFFFAOYAG
  • O=S(=O)=O.n1ccccc1
Properties
C5H5NSO3
Molar mass 159.16 g/mol
Appearance white solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
ROH + C5H5NSO3 → [C5H5NH]+[ROSO3]−

It also is useful for sulfamations:

R2NH + C5H5NSO3 → C5H5N + R2NSO3H

The compound is used for sulfonylation reactions, especially in the sulfonylation of furans.[2] It is also an activating electrophile in a Parikh-Doering oxidation.[3]

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. ^ Spivey, Alan (12 March 2012). "Heteroaromatic Chemistry Lectures 4 and 5" (PDF). Imperial College Research. Retrieved 7 February 2017.
  3. ^ 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.