Fulvalene

  • Bicyclopentyliden -2, 4,2 ', 4'- tetraene
  • 1,1 '- Bi [ cylopentadienyliden ]
  • Pentafulvalen
  • Bicyclopentadienyliden
  • [5,5 '] Bicyclopentadienyliden

Orange liquid

Liquid

Template: Infobox chemical / molecular formula search available

Fulvalene is a chemical compound selected from the group consisting of cycloalkenes. Formally it consists of two cyclopentadiene rings that are linked together by a double bond. Fulvalene is isomeric with naphthalene and azulene.

Representation

The first synthesis trial of fulvalene by oxidative coupling of Cyclopentadienylsalzen with iron ( III) chloride resulted in the discovery of ferrocene.

Fulvalene can be prepared from the reaction of cyclopentadiene with butyllithium. Intermediary a cyclopentadienyl radical is formed, which dimerizes. This is then oxidized by oxygen to fulvalene.

Properties

Fulvalene is an orange liquid. The compound is unstable and goes with dimerization Diels -Alder reactions and [2 2 ] cycloaddition reactions a. Relatively stable is the electron-deficient Perchlorfulvalen ( C10Cl8 ). Tetrathiafulvalene ( C6H4S4 ) is an organic semiconductor.

CAS registry number Iron(III) chloride N-Butyllithium Diels–Alder reaction
355545
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