Pyridine → Dibenzo[cd,lm]perylene

HRID 6576Notes

Reaction equation

HRID 6576 reaction equation
[CH2:1]1[C:10]2=[CH:11][CH:12]=[CH:13][C:8]3=[C:9]2[C:4](=[CH:5][CH:6]=[CH:7]3)[CH:3]=[CH:2]1.N1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[Zn].C(O)(=O)C>[CH:6]1[CH:5]=[C:4]2[CH:3]=[CH:2][C:1]3[C:1]4[CH:10]=[CH:9][C:4]5=[CH:5][CH:6]=[CH:19][C:18]6=[C:3]5[C:2]=4[C:15]([CH:16]=[CH:17]6)=[C:11]4[CH:12]=[CH:13][C:8](=[C:9]2[C:10]=34)[CH:7]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 9149Phenalene

Product 1

HCID 9103Dibenzo[cd,lm]perylene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

With reference to the following scheme, perinaphthene and zinc powder were added to pyridine (I in the following synthesis scheme), 50 ml of 80% acetic acid was added dropwise thereto with stirring under reflux in nitrogen flow over five hours, the resulting precipitate (II in the following synthesis scheme I) was filtrated, was dehydrated and sublimated using a vacuum sublimation apparatus and thereby yielded unsubstituted peropyrene (III in the following synthesis scheme).

Workup

  1. additionwas added dropwise
  2. temperatureunder reflux in nitrogen flow over five hours
  3. filtrationwas filtrated

Sources & evidence

ORD record
ord-747a39fbf3734e7585c10393e8a4c1b7
Source dataset
uspto-grants-2006_08
Patent number
US07083867B2

Reaction notes

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