A novel route to spin-labeled dihydrooxepines and o-benzoquinones View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2011-11

AUTHORS

E. V. Tretyakov, S. E. Tolstikov, G. V. Romanenko, A. S. Bogomyakov, V. K. Cherkasov, D. V. Stass, V. I. Ovcharenko

ABSTRACT

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. More... »

PAGES

2325-2330

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-011-0356-8

DOI

http://dx.doi.org/10.1007/s11172-011-0356-8

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1043395732


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