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Synthesis and reactivity of 3-methylsulfinyl-2H-cyclohepta[b]furan-2-ones.

  作者 Higashi, Junya;Okada, Kazuyuki;Shoji, Taku;Toyota, Kozo;Watanabe, Masataka;Yasunami, Masafumi;Kikuchi, Shigeru;Ito, Shunji;Morita, Noboru;  
  选自 期刊  Heterocycles;  卷期  2008年76-1;  页码  759-770  
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[摘要]2H-Cyclohepta[b]furan-2-one (I) reacted with Me2S.(HO3SCF3)2 to give dimethyl(2-oxo-2H-cyclohepta[b]fur-3-yl)sulfonium triflate, which was treated with Et3N to give 3-methylthio-2H-cyclohepta[b]furan-2-one. The latter sulfide was oxidized with m-CPBA to give the corresponding sulfoxide and sulfone. The sulfoxide thermally underwent coupling reaction to give 3,3'-bi-2H-cyclohepta[b]furan-2-one. The sulfoxide reacted with triflic anhydride to afford the resp. sulfonium ion at lower temp., which reacted with I to give the corresponding dicycloheptafurylsulfonium salt. Subsequent treatment with Et2NH or Et3N gave the corresponding thioether.

 
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