HIST 19 |
| Organoaminoxyl radicals, commonly referred to as nitroxyls or nitroxides, have found widespread use as radical traps and spin labels. The first stable example, diphenylnitroxide, was reported in 1914 by H. Wieland. While aromatic analogues followed, it was not until 1959 that O. L. Lebedev reported the preparation of the cycloaliphatic 2,2,6,6-tetramethylpiperidine-N-oxide (TEMPO). Work on cycloaliphatic systems was then continued by E. G. Rozantsev. As the original TEMPO work was published in provincial Russian sources, it was not until Rozantsev started publishing in international journals that this work became of notice. Between the original TEMPO preparation and its discovery by the scientific community, A. K. Hoffmann reported the preparation of di-t-butylnitroxide in 1961. Finally, A. Rassat explained the instability of most nitroxides in the mid 1960s, laying out the requirements for future stable systems. The work of these groups in the development of this class of organic radicals will be presented. |
|
Landmark Stable Free Radicals of the 20th Century
8:30 AM-12:05 PM, Monday, March 26, 2007 Hyatt Regency McCormick -- 20C, Oral
Division of the History of Chemistry |