1394867-16-3Relevant articles and documents
A novel route to spin-labeled dihydrooxepines and o-benzoquinones
Tretyakov, E. V.,Tolstikov, S. E.,Romanenko, G. V.,Bogomyakov, A. S.,Ovcharenko, V. I.,Cherkasov, V. K.,Stass, D. V.
, p. 2325 - 2330,6 (2011)
A reaction of a lithiated derivative of 4,4,5,5-tetramethyl-3-oxido-4,5- dihydro-1H-imidazole 1-oxyl with 3,6-di-tert-butyl-o-benzoquinone at -80 °C predominantly gave spin-labeled dihydrooxepine via nucleophilic 1,2-addition of the paramagnetic carbanion to the CO group of the benzoquinone followed by insertion of the O atom into the ring. At lower temperatures, this reaction was accompanied by 1,4-addition of the organolithium compound to the benzoquinone followed by oxidation of the resulting adduct into spin-labeled o-benzoquinone. This one pot process is a novel approach to organic derivatives that can further be converted into di- and polyradicals combining nitronyl nitroxide and semiquinolate fragments.