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Reaction of sodium bis(trimethylsilyl)amide with bromotoluenes

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Abstract

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.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    A. V. Lis, I. P. Tsyrendorzhieva, A. I. Albanov, B. A. Shainyan & V. I. Rakhlin

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  1. A. V. Lis
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  2. I. P. Tsyrendorzhieva
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  3. A. I. Albanov
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  4. B. A. Shainyan
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  5. V. I. Rakhlin
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Correspondence to V. I. Rakhlin.

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Original Russian Text © A.V. Lis, I.P. Tsyrendorzhieva, A.I. Albanov, B.A. Shainyan, V.I. Rakhlin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 3, pp. 353–358.

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Lis, A.V., Tsyrendorzhieva, I.P., Albanov, A.I. et al. Reaction of sodium bis(trimethylsilyl)amide with bromotoluenes. Russ J Org Chem 51, 335–340 (2015). https://doi.org/10.1134/S1070428015030082

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  • DOI: https://doi.org/10.1134/S1070428015030082

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