title: Synthesis of alkylidenephthalans through fluoride-induced cyclization of electron-deficient 2-siloxymethylphenylacetylene derivatives.
abstract: Fluoride-based deprotection of silylated 2-alkynylbenzyl alcohol derivatives featuring carbonyl-substituted alkynes results in the direct synthesis of alkylidenephthalan vinylogous esters. The reaction is selective for the Z alkylidenephthalans in a thermodynamically controlled process. Similar compounds are also produced in the coupling of Fischer carbene complexes with 2-alkynylbenzoyl derivatives in an aqueous solvent system. Subsequent acid-catalyzed inter- or intramolecular Diels-Alder reactions lead to hydronaphthalene or hydrophenanthrene derivatives.
authors.affiliation: Department of Chemistry and Biochemistry, New Mexico State University, Las Cruces, New Mexico 88003, USA.
authors.forename: Shaofeng
authors.initials: S
authors.lastname: Duan
authors.forename: Karen
authors.initials: K
authors.lastname: Cress
authors.forename: Kris
authors.initials: K
authors.lastname: Waynant
authors.forename: Elias
authors.initials: E
authors.lastname: Ramos-Miranda
authors.forename: James W
authors.initials: JW
authors.lastname: Herndon