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Title: Synthesis of gem -difluoromethylenated polycyclic cage compounds
Authors: Chonticha Masusai
Darunee Soorukram
Chutima Kuhakarn
Patoomratana Tuchinda
Chaveng Pakawatchai
Saowanit Saithong
Vichai Reutrakul
Manat Pohmakotr
Mahidol University
Prince of Songkla University
Keywords: Chemistry
Issue Date: 6-Feb-2015
Citation: Journal of Organic Chemistry. Vol.80, No.3 (2015), 1577-1592
Abstract: © 2015 American Chemical Society. The synthesis of gem-difluoromethylenated polycyclic cage compounds, utilizing PhSCF2SiMe3 as a gem-difluoromethylene building block, is described. The fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to both maleic anhydride-cyclopentadiene and maleic anhydride-cyclohexadiene adducts was accomplished with high stereoselectivity to provide the corresponding adducts that were treated with Grignard reagents, followed by acid-catalyzed lactonization to afford the corresponding γ-butyrolactones, each as a single isomer. These γ-butyrolactones underwent intramolecular radical cyclization to give the corresponding tetracyclic cage γ-butyrolactones, which were employed as precursors for the synthesis of gem-difluoromethylenated tetracyclic cage lactols or tetracyclic cage furans, upon treatment with Grignard reagents.
ISSN: 15206904
Appears in Collections:Scopus 2011-2015

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