Abstract
Acid-catalyzed reaction of trifluoromethanesulfonamide with paraformaldehyde in ethyl acetate led to the formation of oxymethylated products that did not form in the reaction carried out in sulfuric acid. Following products were obtained: 5-trifluoromethylsulfonyl-1,3-dioxazinane, 3,7-bis-(trifluoromethylsulfonyl)-1,5,3,7-dioxadiazocane, and a complex of trifluoromethanesulfonamide with 2,4,8,10-tetraoxospiro[5,5]undecene, 1:1. The spiroring resulted from the cyclization of pentaerythritol under the action of formaldehyde. The pentaerythritol formed in its turn by oxymethylation of the methyl group of ethyl acetate with paraformaldehyde followed by the reduction of the COOEt group into CH2 OH by the formaldehyde.
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Original Russian Text © V.I. Meshcheryakov, M.Yu. Moskalik, A. Kelling, U. Schilde, I.A. Ushakov, B.A. Shainyan, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 2, pp. 313–317.
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Meshcheryakov, V.I., Moskalik, M.Y., Kelling, A. et al. Oxymethylation of trifluoromethanesulfonamide with paraformaldehyde in ethyl acetate. Russ J Org Chem 44, 311–316 (2008). https://doi.org/10.1134/S1070428008020206
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DOI: https://doi.org/10.1134/S1070428008020206