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Bergman Cyclization

March 2, 2013

The Bergman cyclizationalso known as the Bergman cycloaromatization, is a thermal, photochemical, or metal-mediated cycloaromatization of enediynes that provides access to substituted arenes. The cyclization initially forms a 1,4-benzenediyl diradical which , being highly reactive, reacts with hydrogen donor, such as 1,4-cyclohexadiene, to give an arene.

This reaction is named after a American chemist Robert George Bergman in 1942.

Bergman cyclization

Mechanism of the reaction

  • This reaction takes place under thermal condition involved the initial generation of a 1,4-benzenediyl diradical species known as para-benzyne.
  • 1,4-benzenediyl diradical – a highly reactive species, that reacts with a H• donor to give the corresponding arenes.
  • 2,6,10,14-tetramethylpentadecane, benzene is formed suggesting that hydrocarbon solvent acts as a hydrogen atom donor to quench the diradical intermediate.

Bergman cyclization mechanism


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