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

HRID 1073326Notes

Reaction equation

HRID 1073326 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[N:15][NH2:16])[C:4]=2[CH:3]=1>O1CCCC1.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[N+:15]=[N-:16])[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 539104042-Fluoro-9-fluorenone hydrazone

Product 1

HCID 128716112-Fluoro-9-diazofluoreneYield 101%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. filtrationThe reaction was then filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6254d639a8834cb99ca0a08b23fd4c67
Source dataset
uspto-grants-1990_11
Patent number
US04968809

Reaction notes

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