Intermolecular [4 + 2] cycloaddition of o-quinodimethanes derived from ene-bis(sulfinylallenes).
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.
Kitagaki
Shinji
S
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
Katoh
Kumiko
K
Ohdachi
Kazuhiro
K
Takahashi
Yuji
Y
Shibata
Daisuke
D
Mukai
Chisato
C
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*
D011084:Polycyclic Aromatic Hydrocarbons; D011809:Quinones; D013457:Sulfur Compounds; D008697:Methane