Thermal decay of TEMPO in acidic media via an N-oxoammonium salt intermediate†
Yun Ma,Colin Loyns,Peter Price,Victor Chechik
Organic & Biomolecular Chemistry Pub Date : 05/13/2011 00:00:00 , DOI:10.1039/C1OB05475A
Abstract

Disproportionation of TEMPO in acids leads to the formation of an N-oxoammonium salt, which can further decompose under thermal conditions, yielding the corresponding hydroxylamine, N2O, CO2 and a series of dimerisation products. Overall, acid-catalysed thermal decay of TEMPO leads to ca. 80% yield of hydroxylamine.

Graphical abstract: Thermal decay of TEMPO in acidic media via an N-oxoammonium salt intermediate