title: Intermolecular [4 + 2] cycloaddition of o-quinodimethanes derived from ene-bis(sulfinylallenes).
abstract: Intermolecular [4 + 2] cycloaddition of o-quinodimethanes, prepared in situ from ene-bis(propargyl alcohols) and benzenesulfenyl chloride via ene-bis(sulfinylallene) formation, was investigated. Benzene-bridged bis(propargyl alcohols) reacted with both electron-deficient and electron-rich olefins to give the corresponding [4 + 2] cycloadducts. Ethylene-bridged bis(propargyl alcohols) underwent similar cycloaddition with electron-deficient olefins. Construction of some heterocycles based on the newly developed sequential reaction is also described.
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. kitagaki@p.kanazawa-u.ac.jp
authors.forename: Shinji
authors.initials: S
authors.lastname: Kitagaki
authors.forename: Kumiko
authors.initials: K
authors.lastname: Katoh
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Ohdachi
authors.forename: Yuji
authors.initials: Y
authors.lastname: Takahashi
authors.forename: Daisuke
authors.initials: D
authors.lastname: Shibata
authors.forename: Chisato
authors.initials: C
authors.lastname: Mukai
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D008697:Methane / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*; D011809:Quinones / Q000737:chemistry*; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D011084:Polycyclic Aromatic Hydrocarbons; D011809:Quinones; D013457:Sulfur Compounds; D008697:Methane