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Cascade Transformations of Trifluoromethanesulfonamide in Reaction with Formaldehyde

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Abstract

Trifluoromethanesulfonamide reacts with paraformaldehyde in acid medium to give both open-chain and cyclic condensation products: bis(trifluoromethylsulfonylamino)methane, N, N-bis(trifluoromethylsulfonylaminomethyl)trifluoromethanesulfonamide, 5-(trifluoromethylsulfonyl)dihydro-1,3,5-dioxazine, 3,5-bis(trifluoromethylsulfonyl)tetrahydro-1,3,5-oxadiazine, 1,3,5-tris(trifluoromethylsulfonyl)hexahydro-1,3,5-triazine, 5,7-bis(trifluoromethylsulfonyl)-1,3,5,7-dioxadiazocane, and 5,7,9-tris(trifluoromethylsulfonyl)-1,3,5,7,9-dioxatriazecane. Amidoalkylation of acetonitrile in the system trifluoromethanesulfonamide-paraformaldehyde-phosphoric acid leads to formation of N-(trifluoromethylsulfonylaminomethyl)acetamide.

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Authors and Affiliations

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

    V. I. Meshcheryakov, A. I. Albanov & B. A. Shainyan

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  1. V. I. Meshcheryakov
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  2. A. I. Albanov
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  3. B. A. Shainyan
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Dedicated to Full Member of the Russian Academy of Sciences N.S. Zefirov on His 70th Anniversary

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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 9, 2005, pp. 1409–1414.

Original Russian Text Copyright © 2005 by Meshcheryakov, Albanov, Shainyan.

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Meshcheryakov, V.I., Albanov, A.I. & Shainyan, B.A. Cascade Transformations of Trifluoromethanesulfonamide in Reaction with Formaldehyde. Russ J Org Chem 41, 1381–1386 (2005). https://doi.org/10.1007/s11178-005-0351-3

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  • DOI: https://doi.org/10.1007/s11178-005-0351-3

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