Sulfamation
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organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
sulfamation is the installation of either of two related
functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
s, sulfamic acid (R2NSO3H) and sulfamate (R2NSO3). Typical methods entail reaction of primary amines with sources of sulfur trioxide such as
pyridine-sulfur trioxide 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 ...
:{{cite journal , doi=10.1021/jo01314a033, title=Sulfonylamine-Mediated Sulfamation of Amines. A Mild, High Yield Synthesis of Sulfamic Acid Salts, year=1980, last1=DuBois, first1=Grant E., last2=Stephenson, first2=Rebecca A., journal=The Journal of Organic Chemistry, volume=45, issue=26, pages=5371–5373 :RNH2 + SO3 → RNHSO3H Sulfamation can also be effected by treating the amine with the sulfate ester of
catechol Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amount ...
(C6H4O2SO2).


References

Sulfur oxoacids Sulfamates