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Synlett 2001; 2001(2): 0293-0295
DOI: 10.1055/s-2001-10792
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Iodotrimethylsilane-induced Cyclization of 6-Alkynal Acetals

Kazuaki Takami* , Hideki Yorimitsu, Hiroshi Shinokubo, Seijiro Matsubara, Koichiro Oshima
  • *Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan; Fax +81-75-753-4863; E-mail: oshima§fm1.kuic.kyoto-u.ac.jp
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Publication Date:
31 December 2001 (online)

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Treatment of 7-phenyl-6-heptynal dimethyl acetal with iodotrimethylsilane afforded 2-(1-iodobenzylidene)cyclohexyl methyl ether via the intramolecular nucleophilic attack of the carbon-carbon triple bond to the oxonium ion generated by the action of iodotrimethylsilane.

iodotrimethylsilane - cyclization - 6-alkynal acetal - oxonium ion - vinyl iodide