ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Spin Trapping. III. Studies of Radical Reactions of a Bicyclic 1-Hydroxy-3-imidazoline-3-oxideRadical addition reactions to the nitrono group and the oxidation of the 8-hydroxy-1,4,5,7-tetramethyl-6,8-diazabicyclo[3.2.1]oct-6-en-6-oxide 2b were investigated by e.s.r.-spectroscopy. Oxidation of 2b by Ag2O, PbO2, hydrogenperoxide, tert.-butoxy and benzoyloxy radicals, respectively, yields a bicyclic nitroxide with typical a(N)-value (1,9 mT). Testing a wide range of carbon-centered radicals we did not find, however, any spin adducts in contrast to the literature. Only H-atoms are found to add to the nitrone function of 2b giving a bicyclic nitroxide 4b (R′ = H) with a(N)-value of 1,4 mT, a(Hax) = 2,4 mT. The relationship between a ring-chain tautomerism of 2 as previously described and the formation of radicals has been demonstrated by radical reactions of derivatives of ring opened isomers 5b.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19863280420
