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Trifluoromethanesulfonamide reacts with paraformaldehyde in acid medium to give both openchain 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.

General remarks 1 H, 13 C and 77 Se NMR spectra were measured on a Bruker AV400 (DPX400) spectrometer at 400 MHz, 100.6 MHz and 76.3 MHz, respectively. 1 H NMR chemical shifts were calibrated by residual proton of CDCl 3 (δ 7.27 ppm). 13 C NMR chemical shifts were calibrated by deuterated carbon of CDCl 3 (δ 77.1 ppm). 77 Se NMR spectra were recorded with diphenyl diselenide (δ 463 ppm) as external standards, relative to dimethyl selenide (δ 0.00 ppm). Mass spectra were measured on an Agilent 5975 with electron impact (EI) ionization at 70 eV. X-ray data were collected on a BRUKER D8 VENTURE PHOTON 100 CMOS diffractometer with MoK α radiation (λ = 0.71073 Å) using the φ and ω scans technique. The structures were solved and refined by direct methods using the SHELX [Sheldrick, G. M. Acta Crystallogr. 2008, 64, 112]. Data were corrected for absorption effects using the multi-scan method (SADABS). All non-hydrogen atoms were refined anisotropically using SHELX. The coordinates of the hydrogen atoms were calculated from geometrical positions. Crystal data and experimental details are given in Table S2. А one-pot synthesis of 2-bromomethyl-1,3-thiaselenole (1) Se S Br

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