Sulfur trioxide pyridine complex explained

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 → [C<sub>5</sub>H<sub>5</sub>NH]+[ROSO<sub>3</sub>]−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

  1. Thomas T. Tidwell "Sulfur Trioxide–Pyridine" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. . Article Online Posting Date: April 15, 2001
  2. Web site: Heteroaromatic Chemistry Lectures 4 and 5. Spivey. Alan. 12 March 2012. Imperial College Research. 7 February 2017.
  3. Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide . Jekishan R. Parikh, William v. E. Doering . . 1967 . 89 . 5505–5507 . 10.1021/ja00997a067 . 21.

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Sulfur trioxide pyridine complex".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.