title: Syntheses and reactivity of naphthalenyl-substituted arenediynes.
abstract: A series of naphthalenyl-substituted arenediynes were prepared to examine photochemical reactivity. For naphthalen-1-ylethynyl arenediyne, 350 nm photolysis resulted in a tandem [2 + 2] photocycloaddition to afford cyclobutene adducts. For naphthalen-2-ylethynyl derivatives, electron-donating methoxy substituents were found to facilitate C(1)-C(6) Bergman cyclization at 300 nm. Theoretical calculations provided further insight into thermal and photochemical reactivity.
authors.affiliation: Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, California 95819, USA.
authors.forename: Nadezhda V
authors.initials: NV
authors.lastname: Korovina
authors.forename: Michael L
authors.initials: ML
authors.lastname: Chang
authors.forename: Trang T
authors.initials: TT
authors.lastname: Nguyen
authors.forename: Ramiro
authors.initials: R
authors.lastname: Fernandez
authors.forename: Heather J
authors.initials: HJ
authors.lastname: Walker
authors.forename: Marilyn M
authors.initials: MM
authors.lastname: Olmstead
authors.forename: Benjamin F
authors.initials: BF
authors.lastname: Gherman
authors.forename: John D
authors.initials: JD
authors.lastname: Spence
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D053280:Diynes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D053280:Diynes; D009281:Naphthalenes