title: Intramolecular [4 + 2] trapping of a hexadehydro-Diels-Alder (HDDA) benzyne by tethered arenes.
abstract: We report here the efficient, intramolecular trapping in a Diels-Alder (DA) sense of thermally generated benzynes by one of two pendant arene rings. A more electron-rich ring (p-methoxyphenyl) reacted substantially faster than a simple phenyl ring, which was, in turn, slightly more reactive vs a 4-carbomethoxyphenyl ring. Photoinduced di-π-methane rearrangement of the initial DA adducts gave rise to unusual isomeric polycyclic adducts.
authors: Department of Chemistry, University of Minnesota , 207 Pleasant Street, SE Minneapolis, Minnesota 55455, United States.
authors: Vedamayee D
authors: VD
authors: Pogula
authors: Tao
authors: T
authors: Wang
authors: Thomas R
authors: TR
authors: Hoye
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D061565:Cycloaddition Reaction; D004583:Electrons; D007536:Isomerism; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D011083:Polycyclic Compounds; C524146:benzyne