Reaction #6672

ord-747a39fbf3734e7585c10393e8a4c1b7

Reaction equation

C1=Cc2cccc3cccc(c23)C1
perinaphthene
c1ccncc1
pyridine
→
c1cc2ccc3c4ccc5cccc6ccc(c7ccc(c1)c2c37)c4c56
peropyrene

Reactants

—
II
C1=Cc2cccc3cccc(c23)C1
perinaphthene
c1ccncc1
pyridine

Reagents

[Zn]
zinc

Solvents

CC(=O)O
acetic acid

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added dropwise
  2. 2
    Temperatureunder reflux in nitrogen flow over five hours
  3. 3
    Filtrationwas filtrated

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07083867B2uspto-grants-2006_08