Azobisisobutyronitrile → Fluorene

HRID 1496785Notes

Reaction equation

HRID 1496785 reaction equation
COCCOCC[C:8]1(CCOCCOC)[C:20]2[CH:19]=[C:18](C=C)[CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][C:11](C=C)=[CH:12][CH:13]=2.CC(N=NC(C#N)(C)C)(C#N)C>O.C1COCC1>[CH:10]1[C:9]2[CH2:8][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 86676055HCID 86676055, compound

Product 1

HCID 6853Fluorene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of the polymeric macroinitiator, 7 (2.0 g, 0.22 mmol, Mw) 7700, PDI) 1.11), 3 (0.668 g, 1.55 mmol), and AIBN (0.43 mg, 0.03 mmol) was dissolved in 2% H2O in THF (6.0 mL), degassed by four freeze/pump/thaw cycles, and sealed under argon. The polymerization mixture was then stirred at 85° C. for 48 h and allowed to cool, and the star polymer, 23, was obtained after precipitation using ethyl acetate followed by dialysis against methanol (1.9 g, 71%, Mw) δ 500, PDI) 1.32). 1H NMR (CDCl3): δ (ppm) 7.10-7.28 (br m, ArH), 5.03 (br s, CH), 4.35 (br s, CH2), 2.68 (br s, CH2), 2.42 (br s, CH2), 1.95 (br s, CH2), 1.50-1.85 (br m, CH2).

Workup

  1. customdegassed by four freeze/pump/thaw cycles
  2. customsealed under argon
  3. temperatureto cool
  4. customthe star polymer, 23, was obtained
  5. customafter precipitation
  6. customfollowed by dialysis against methanol (1.9 g, 71%, Mw) δ 500, PDI) 1.32)

Sources & evidence

ORD record
ord-d07f0a1f9253410fb18bea59fe42dec2
Source dataset
uspto-grants-2015_12
Patent number
US09198985B2

Reaction notes

Loading…