caa a22 4500 605529655 CHVBK 20210128100819.0 cr unu---uuuuu 210128e20150301xx s 000 0 eng 10.1134/S1070428015030082 doi (NATIONALLICENCE)springer-10.1134/S1070428015030082 Reaction of sodium bis(trimethylsilyl)amide with bromotoluenes [Elektronische Daten] [A. Lis, I. Tsyrendorzhieva, A. Albanov, B. Shainyan, V. Rakhlin] Isomeric bromotoluenes react with sodium bis(trimethylsilyl)amide through intermediate methylbenzynes, yielding N,N-bis(trimethylsilyl)toluidines and rearrangement products, N,2-bis(trimethylsilyl)toluidines. The formation of the latter is a rare example of 1,3-migration of silyl group from nitrogen atom to aromatic carbon atom. The rearrangement is favored by increased solvent polarity and elevated temperature. The observed product ratio can be rationalized by DFT quantum chemical calculations. Pleiades Publishing, Ltd., 2015 Lis A. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Tsyrendorzhieva I. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Albanov A. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Shainyan B. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Rakhlin V. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut Russian Journal of Organic Chemistry Pleiades Publishing 51/3(2015-03-01), 335-340 1070-4280 51:3<335 2015 51 11178 https://doi.org/10.1134/S1070428015030082 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1134/S1070428015030082 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Lis A. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 700 1- Tsyrendorzhieva I. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 700 1- Albanov A. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 700 1- Shainyan B. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 700 1- Rakhlin V. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, 664033, Irkutsk, Russia aut NATIONALLICENCE 773 0- Russian Journal of Organic Chemistry Pleiades Publishing 51/3(2015-03-01), 335-340 1070-4280 51:3<335 2015 51 11178