2-Fluoro-9-fluorenone hydrazone → 2-Fluoro-9-diazofluorene

Participants

Reaction Steps

A mixture of (12) (6.5 g, 30.6 mmoL) and activated manganese dioxide (13 g, 150 mmoL, 5 eq) in tetrahydrofuran (300 mL) was stirred at room temperature for 18 h. The reaction was then filtered through celite and concentrated to provide 6.5 g (100%) of product (13) as a red solid which was used without further purification. A sample recrystallized from ether/hexane provided the following data: mp 89°-90 ° C.; IR (KBr) 2075, 1180 cm-1 ; 1H NMR (CDCl3, 200 MHz) 7.88-7.79 (m, 2H), 7.49-7.26 (m, 3H), 7.15 (bdd, 1H, J=2.3, 8.9Hz), 7.01 (ddd, 1H, J=2.3, 8.5, 9.3 Hz); MS m/z 210 (M+), 182 (base peak).

Provenance & Evidence