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AZIDO (TEMPO variants)

TEMPO derivatives (i.e., AZADO) and alternatives

A large number of TEMPO variants exist based on the 2, 2, 6, 6,-tetramethylpiperidine motif. In recent years, a number of structurally diverse nitroxide radical oxidation catalysts have appeared. A drawback is lack of commercial availability, although more are becoming commercial or readily prepared. A key feature is that these catalysts often show positive rate enhancements compared to TEMPO – often several orders of magnitude. The mechanism of action is identical, requiring a terminal oxidant like NaOCl to drive the catalytic cycle.


J. Am. Chem. Soc. 2006, 128 (26), 8412–8413.
2-Azaadamantane N-Oxyl (AZADO) and 1-Me-AZADO

Chem. Pharm. Bull. 2011, 59 (12) 1570—1573 (2011).
9-Azanoradamantane N-Oxyl (Nor- AZADO)

Green Chem2011, 13, 1659-1663.
1-methyl-2-azaadamantane N-oxyl

J. Org. Chem. 2009, 74 (12), 4619–4622.
9-Azabicyclo[3.3.1]nonane N-Oxyl (ABNO)