Sulfur trioxide → 3,4,5,5-Tetrafluorothiophen-2(5H)-one

반응식

S(=O)(=O)=[O:2].[F:5][C:6]1([F:15])[S:10][C:9](F)(F)[C:8]([F:13])=[C:7]1[F:14].[F-].FC1(F)SC(F)(F)C=C1>>[F:5][C:6]1([F:15])[S:10][C:9](=[O:2])[C:8]([F:13])=[C:7]1[F:14]

참가 물질

반응물 4

HCID 24682Sulfur trioxide

HCID 28179Fluoride Ion

HCID 10943363Hexafluoro-2,5-dihydrothiophene

HCID 12916665HCID 12916665, 화합물

생성물 1

HCID 151220123,4,5,5-Tetrafluorothiophen-2(5H)-one수율 25%

실험 절차

Sulfur trioxide (128.0 g, 1.60 mol) was added rapidly to 77.6 g (0.40 mol) of hexafluoro-2,5-dihydrothiophene. After an initial exotherm, the mixture was refluxed for 30 min. and fractionated to give 121.9 g, bp 42°-55° C., shown to be mainly pyrosulfuryl fluoride by 19F NMR, and 29.5 g of crude tetrafluoro-2,5-dihydrothiophene, bp 77°-85° C. Redistillation of this product afforded 16.9 g (25%) of tetrafluoro-2,5-dihydrothiophene-2-one, bp 83° C. IR (CCl4): 1755 (C=O) and 1740 cm-1 (C=C). NMR (CCl4): 19Fφ-92.0 (d of d, JFF 14.7, 5.5 Hz, 2F, CF2),-133.5 (q, JFF 14.3 Hz, lF, CF), -144.3 (d of t, JFF 13.9, 5.5 Hz, lF, CF). MS: m/e 171.9615 (M+ ; calcd for C4F4OS, 171.9606), 143 9664 (M+ --CO; cald, 143,9657), 121.9641 (M+ --CF2 ; calcd, 121.9638). Anal. Calcd for C4F4OS: C, 27.91; S, 18.63 Found: C, 28.27; S, 19.16.