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:Thomas T. Tidwell "Sulfur Trioxide–Pyridine" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. . Article Online Posting Date: April 15, 2001 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. It is also an activating electrophile in a Parikh-Doering oxidation.
References