反应详情

To a stirred suspension of triazene 8b (5.63 g, 20 mmol) and anhydrous potassium hexafluorophosphate (3.68 g, 20 mmol) and excess vinyl bromide 11e (10 mL) in dry dichloromethane (100 mL) in the dark at 78° C. is added tert-butyl hypochlorite (3.33 mL, 30 mmol), upon which the mixture instantly darkens. The mixture is stirred overnight as it is slowly allowed to warm to room temperature. The contents are then filtered, and the solid residue is washed with dichloromethane. The filtrate is collected, and volatiles are evaporated under reduced pressure. Diethyl ether is then added, and the mixture is vigorously triturated for ca. 1 hour, with occasional scratching of the glass surfaces to ensure efficient mixing. Filtration and washing with copious quantities of diethyl ether afford, after drying under vacuum, triazolium salt 10be as an off-white solid (8.21 g, 91%). 1H-NMR (CD3CN, 300 MHz): δ=8.82 (s, 2H), 7.21 (s, 4H), 2.40 (s, 6H), 2.09 (s, 12H). 13C-NMR (CD3CN, 75 MHz): δ=144.3, 135.7, 135.1, 132.3, 130.9, 21.4, 17.5. HR-MS (ESI): Calcd. for C20H24N3 [M+]: 306.1965. found 306.1973.

1. filtrationThe contents are then filtered
2. washthe solid residue is washed with dichloromethane
3. customThe filtrate is collected
4. customvolatiles are evaporated under reduced pressure
5. additionDiethyl ether is then added
6. customthe mixture is vigorously triturated for ca. 1 hour
7. filtrationFiltration
8. washwashing with copious quantities of diethyl ether
9. customafford
10. dry with materialafter drying under vacuum, triazolium salt 10be as an off-white solid (8.21 g, 91%)