title: A novel stereoselective [8+2] double cycloaddition route to hydronaphthalene ring systems.
abstract: Substituted hydronaphthalenes where each of the ten carbons of the two-ring system contains functionality were obtained through a tandem [8+2] cycloaddition and base-catalyzed rearrangement process using dienylfurans and electron-deficient alkynes. If the [8+2] process is conducted under solvent-free conditions the process could be conducted in a single reaction flask without isolation of the chromatographically sensitive [8+2] cycloadducts. A mechanism involving base catalysed alkene positional isomerization followed by disrotatory electrocyclic ring closure was proposed for the key reaction step that converts [8+2] cycloadducts to hydronaphthalenes. The products undergo selective ring opening-isomerization processes upon treatment with Lewis acids.
authors: Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003 USA.
authors: Weijiang
authors: W
authors: Ying
authors: Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003 USA.
authors: Lei
authors: L
authors: Zhang
authors: Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003 USA.
authors: Paul A
authors: PA
authors: Wiget
authors: Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, NM 88003 USA.
authors: James W
authors: JW
authors: Herndon