A novel route to spin-labeled dihydrooxepines and o-benzoquinones

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

Journal

Russian Chemical Bulletin
ISSN: 1066-5285

Output data

Year: 2011, Volume: 60, Number: 11, Pages: 2325-2330 Pages count : 6 DOI: 10.1007/s11172-011-0356-8

Authors

Tretyakov E.V. ¹ , Tolstikov S.E. ¹ , Romanenko G.V. ¹ , Bogomyakov A.S. ¹ , Cherkasov V.K. ² , Stass D.V. ³ , Ovcharenko V.I. ¹

Affiliations

1	International Tomography Center, Siberian Branch of the Russian Academy of Sciences
2	G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences
3	Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 ul. Institutskaya, 630090 Novosibirsk, Russian Federation

A reaction of a lithiated derivative of 4,4,5,5 tetramethyl 3oxido4,5dihydro1H imid azole 1oxyl with 3,6di tert butyl o benzoquinone at –80 °C predominantly gave spin labeled dihydrooxepine via nucleophilic 1,2addition 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 1,4addition of the organolithium compound to the benzo quinone 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.

Tretyakov E.V. , Tolstikov S.E. , Romanenko G.V. , Bogomyakov A.S. , Cherkasov V.K. , Stass D.V. , Ovcharenko V.I.
A novel route to spin-labeled dihydrooxepines and o-benzoquinones
Russian Chemical Bulletin. 2011. V.60. N11. P.2325-2330. DOI: 10.1007/s11172-011-0356-8 WOS Scopus

Web of science:	WOS:000307517100026
Scopus:	2-s2.0-84865460106

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