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.
Keywords
Formaldehyde Organic Chemistry Acetonitrile Paraformaldehyde Acid MediumPreview
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