In a catalytic cycle with sodium hypochlorite as the stoichiometric oxidant, hypochlorous acid generates the N-oxoammonium salt from TEMPO.
[8] TEMPO oxidations also exhibit chemoselectivity, being inert towards secondary alcohols, but the reagent will convert aldehydes to carboxylic acids.
[9] In cases where secondary oxidizing agents cause side reactions, it is possible to stoichiometrically convert TEMPO to the oxoammonium salt in a separate step.
However, the linkage between the polymer chain and TEMPO is weak, and can be broken upon heating, which then allows the polymerization to continue.
Thus, the chemist can control the extent of polymerization and also synthesize narrowly distributed polymer chains.
[13] Industrial-scale examples of TEMPO-like compounds include hindered amine light stabilizers and polymerisation inhibitors.