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N-sulfinylanilines as dienes in the Diels-Alder reaction. Structural aspects

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Abstract

Reactions of N-sulfinylanilines with norbornene and norbornadiene result in the Diels-Alder adducts of benzo-ortho-thiazine structure, which was confirmed by the NMR, IR spectroscopy and XRD analysis. In all cases the diene added to the norbornenes bicyclic system at the side of the endo-methylene bridge. The methyl group of meta-N-sulfinyl toluidine directs the norbornene entry into the para-position.

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Authors and Affiliations

  1. Kant Russian State University, ul. Universitetskaya 2, Kaliningrad, 236040, Russia

    Ya. V. Veremeichik, P. V. Merabov & V. V. Plemenkov

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Tatarstan, Russia

    O. A. Lodochnikova, D. B. Krivolapov & I. A. Litvinov

  3. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, Russia

    L. V. Spirikhin & A. N. Lobov

Authors
  1. Ya. V. Veremeichik
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  2. P. V. Merabov
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  3. O. A. Lodochnikova
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  4. D. B. Krivolapov
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  5. I. A. Litvinov
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  6. L. V. Spirikhin
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  7. A. N. Lobov
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  8. V. V. Plemenkov
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Correspondence to Ya. V. Veremeichik.

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Original Russian Text © Ya.V. Veremeichik, P.V. Merabov, O.A. Lodochnikova, D.B. Krivolapov, I.A. Litvinov, L.V. Spirikhin, A.N. Lobov, V.V. Plemenkov, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 8, pp. 1343–1348.

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Veremeichik, Y.V., Merabov, P.V., Lodochnikova, O.A. et al. N-sulfinylanilines as dienes in the Diels-Alder reaction. Structural aspects. Russ J Gen Chem 82, 1416–1420 (2012). https://doi.org/10.1134/S1070363212080130

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  • DOI: https://doi.org/10.1134/S1070363212080130

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