Sulfur trioxide pyridine complex

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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 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

↑ Thomas T. Tidwell "Sulfur Trioxide–Pyridine" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. Script error: No such module "doi".. Article Online Posting Date: April 15, 2001
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[1] Thomas T. Tidwell "Sulfur Trioxide–Pyridine" Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley & Sons. Script error: No such module "doi".. Article Online Posting Date: April 15, 2001

[2] Script error: No such module "citation/CS1".

[3] Script error: No such module "Citation/CS1".

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Sulfur trioxide pyridine complex

References

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