Sulfite ester

A sulfite ester is a functional group with the structure (RO)(R'O)SO. When substituents R and R' differ, the compound is chiral owing to the stereogenic sulfur centre. They are commonly prepared by the reaction of thionyl chloride with alcohols in the presence of a base such as pyridine:[1]

2 ROH + SOCl2 + 2 C5H5N → (RO)2SO + 2 C5H5NH+Cl-

The pesticide endosulfan is a sulfite ester. Some simple members include ethylene sulfite, dimethyl sulfite, and diphenylsulfite. Many examples have been prepared from diols, such as sugars.

References

  1. ^ McCormack, W. B.; Lawes, B. C. "Sulfuric and sulfurous esters" Kirk-Othmer Encycl. Chem. Technol., 3rd Ed. (1983), 22, 233-54.doi:10.1002/0471238961.1921120613030315.a01