title: The Phenol-Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics.
abstract: Benzynes produced thermally by the cycloisomerization of triyne-containing precursors [i.e., by the hexadehydro-Diels-Alder (HDDA) reaction] react with phenols at the carbon ortho to the hydroxyl in an enelike fashion. Following tautomerization of the intermediate cyclohexadienones, this produces biaryl derivatives. DFT calculations of model reactions support this mechanistic interpretation. Substituted, unsymmetrical phenols and bis-phenols react in a fashion that can be explained by engagement of the most readily available (non-hydrogen-bonded) hydroxyl in the phenol-ene process.
authors: Department of Chemistry; University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
authors: Juntian
authors: J
authors: Zhang
authors: Department of Chemistry; University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
authors: Dawen
authors: D
authors: Niu
authors: Department of Chemistry; University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
authors: Vincent A
authors: VA
authors: Brinker
authors: Department of Chemistry; University of Minnesota , 207 Pleasant Street, SE, Minneapolis, Minnesota 55455, United States.
authors: Thomas R
authors: TR
authors: Hoye
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D008968:Molecular Conformation; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001555:Benzene Derivatives; D010636:Phenols; C524146:benzyne