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Sulfur trioxide pyridine complex

Sulfur trioxide pyridine complex is the compound with the formula C<sub>5</sub>H<sub>5</sub>NSO<sub>3</sub>. 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:

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

It also is useful for sulfamations:

R<sub>2</sub>NH + C<sub>5</sub>H<sub>5</sub>NSO<sub>3</sub> → C<sub>5</sub>H<sub>5</sub>N + R<sub>2</sub>NSO<sub>3</sub>H

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

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