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- Bergman_cyclization abstract "The Bergman cyclization or Bergman reaction or Bergman cycloaromatization is an organic reaction and more specifically a rearrangement reaction taking place when an enediyne is heated in presence of a suitable hydrogen donor (Scheme 1). It is the most famous and well-studied member of the general class of cycloaromatization reactions. It is named for the American chemist Robert George Bergman (b. 1942). The reaction product is a derivative of benzene.The reaction proceeds by a thermal reaction or pyrolysis (above 200 °C) forming a short-lived and very reactive para-benzyne biradical species. It will react with any hydrogen donor such as 1,4-cyclohexadiene which converts to benzene. When quenched by tetrachloromethane the reaction product is a 1,4-dichlorobenzene and with methanol the reaction product is benzyl alcohol.When the enyne moiety is incorporated into a 10-membered hydrocarbon ring (e.g. cyclodeca-3-ene-1,5-diyne in scheme 2) the reaction, taking advantage of increased ring strain in the reactant, is possible at the much lower temperature of 37 °C. Naturally occurring compounds such as calicheamicin contain the same 10-membered ring and are found to be cytotoxic. These compounds generate the diradical intermediate described above which can cause single and double stranded DNA cuts. There are novel drugs which attempt to make use of this property, including monoclonal antibodies such as mylotarg.A biradical mechanism is also proposed for the formation of certain biomolecules found in marine sporolides that have a chlorobenzene unit as part of their structure. In this mechanism a halide salt provides the halogen. A model reaction with the enediyene cyclodeca-1,5-diyn-3-ene, lithium bromide as halogen source and acetic acid as hydrogen source in DMSO at 37 °C supports the theory:The reaction is found to be first-order in enediyne with the formation of p-benzyne A as the rate-limiting step. The halide ion then donates its two electrons in the formation of a new Br-C bond and radical electron involved is believed to shuttle over a transient C1-C4 bond forming the anion intermediate B. The anion is a powerful base, stripping protons even from DMSO to final product. The dibromide or dihydrogen product (tetralin) never form.As reported in Nature Chemistry, scientists from IBM Research and CiQUS at the University of Santiago de Compostela, demonstrated a reversible Bergman cyclisation for the first time using an atomic force microscope.When learning about the demonstration Bergman commented, \"When we first reported this reaction I had no idea that it would be biologically relevant, or that the reaction could someday be visualized at the molecular level.".
- Bergman_cyclization thumbnail Bergman_cyclization_revised.png?width=300.
- Bergman_cyclization wikiPageExternalLink frame.htm.
- Bergman_cyclization wikiPageID "4098482".
- Bergman_cyclization wikiPageLength "6147".
- Bergman_cyclization wikiPageOutDegree "40".
- Bergman_cyclization wikiPageRevisionID "705394511".
- Bergman_cyclization wikiPageWikiLink 1,4-Cyclohexadiene.
- Bergman_cyclization wikiPageWikiLink 1,4-Dichlorobenzene.
- Bergman_cyclization wikiPageWikiLink Acetic_acid.
- Bergman_cyclization wikiPageWikiLink Aryne.
- Bergman_cyclization wikiPageWikiLink Atomic-force_microscopy.
- Bergman_cyclization wikiPageWikiLink Benzene.
- Bergman_cyclization wikiPageWikiLink Benzyl_alcohol.
- Bergman_cyclization wikiPageWikiLink Bergman_cyclization.
- Bergman_cyclization wikiPageWikiLink Biomolecule.
- Bergman_cyclization wikiPageWikiLink Calicheamicin.
- Bergman_cyclization wikiPageWikiLink Carbon_tetrachloride.
- Bergman_cyclization wikiPageWikiLink Category:Carbon-carbon_bond_forming_reactions.
- Bergman_cyclization wikiPageWikiLink Category:Name_reactions.
- Bergman_cyclization wikiPageWikiLink Category:Rearrangement_reactions.
- Bergman_cyclization wikiPageWikiLink Cytotoxicity.
- Bergman_cyclization wikiPageWikiLink DNA.
- Bergman_cyclization wikiPageWikiLink Dimethyl_sulfoxide.
- Bergman_cyclization wikiPageWikiLink Drug.
- Bergman_cyclization wikiPageWikiLink Enediyne.
- Bergman_cyclization wikiPageWikiLink Enyne.
- Bergman_cyclization wikiPageWikiLink Gemtuzumab_ozogamicin.
- Bergman_cyclization wikiPageWikiLink IBM_Research.
- Bergman_cyclization wikiPageWikiLink Ion.
- Bergman_cyclization wikiPageWikiLink Lithium_bromide.
- Bergman_cyclization wikiPageWikiLink Methanol.
- Bergman_cyclization wikiPageWikiLink Monoclonal_antibody.
- Bergman_cyclization wikiPageWikiLink Non-Kekulé_molecule.
- Bergman_cyclization wikiPageWikiLink Order_of_reaction.
- Bergman_cyclization wikiPageWikiLink Organic_reaction.
- Bergman_cyclization wikiPageWikiLink Pyrolysis.
- Bergman_cyclization wikiPageWikiLink Rate-determining_step.
- Bergman_cyclization wikiPageWikiLink Rearrangement_reaction.
- Bergman_cyclization wikiPageWikiLink Ring_strain.
- Bergman_cyclization wikiPageWikiLink Sporolides.
- Bergman_cyclization wikiPageWikiLink Tetralin.
- Bergman_cyclization wikiPageWikiLink University_of_Santiago_de_Compostela.
- Bergman_cyclization wikiPageWikiLink File:Bergman_cyclization_nuclSubst.png.
- Bergman_cyclization wikiPageWikiLink File:Bergman_cyclization_revised.png.
- Bergman_cyclization wikiPageWikiLink File:Bergman_ring.png.
- Bergman_cyclization wikiPageWikiLinkText "Bergman cyclization".
- Bergman_cyclization wikiPageWikiLinkText "Bergman reaction".
- Bergman_cyclization name "Bergman cyclization".
- Bergman_cyclization namedafter "Robert George Bergman".
- Bergman_cyclization type "Ring forming reaction".
- Bergman_cyclization wikiPageUsesTemplate Template:Reactionbox.
- Bergman_cyclization wikiPageUsesTemplate Template:Reactionbox_Identifiers.
- Bergman_cyclization wikiPageUsesTemplate Template:Reflist.
- Bergman_cyclization subject Category:Carbon-carbon_bond_forming_reactions.
- Bergman_cyclization subject Category:Name_reactions.
- Bergman_cyclization subject Category:Rearrangement_reactions.
- Bergman_cyclization hypernym Reaction.
- Bergman_cyclization type Disease.
- Bergman_cyclization type Scientist.
- Bergman_cyclization type Eponym.
- Bergman_cyclization type Reaction.
- Bergman_cyclization type Scientist.
- Bergman_cyclization comment "The Bergman cyclization or Bergman reaction or Bergman cycloaromatization is an organic reaction and more specifically a rearrangement reaction taking place when an enediyne is heated in presence of a suitable hydrogen donor (Scheme 1). It is the most famous and well-studied member of the general class of cycloaromatization reactions. It is named for the American chemist Robert George Bergman (b. 1942).".
- Bergman_cyclization label "Bergman cyclization".
- Bergman_cyclization sameAs Q819992.
- Bergman_cyclization sameAs Bergman-Cyclisierung.
- Bergman_cyclization sameAs Ciclación_de_Bergman.
- Bergman_cyclization sameAs Réaction_de_Bergman.
- Bergman_cyclization sameAs 正宗・バーグマン環化.
- Bergman_cyclization sameAs m.0bhxj8.
- Bergman_cyclization sameAs Q819992.
- Bergman_cyclization sameAs 伯格曼环化反应.
- Bergman_cyclization wasDerivedFrom Bergman_cyclization?oldid=705394511.
- Bergman_cyclization depiction Bergman_cyclization_revised.png.
- Bergman_cyclization isPrimaryTopicOf Bergman_cyclization.