Stable Sulfur Ylides: XII: Reaction of 3-Alkyl(aryl)thio-silyloxydienes Derived from Stable Sulfur Ylides with Aromatic Aldehydes: Synthesis and Structure of Thiolanium Ylides

Jun etsu Igarashi, Noriyuki Watanabe, Toshio Kinoshita, Sunao Furukawa, Koreharu Ogata

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    Abstract

    The Lewis acid-catalyzed cyclocondensation of methylthio (or phenylthio)-silyloxydienes (2), easily derived from stable sulfur ylides (1), with several aromatic aldehydes (3) was investigated. Namely, in the case of boron trifluoride normal reaction products, 2,3-dihydro-4-pyrones (4), were obtained in good yields. Novel reaction products, thiolanium ylides (6 and 7), were obtained in the presence of titanium(IV) chloride. The structures of 6g was established by X-ray crystallography.

    Original languageEnglish
    Pages (from-to)329-335
    Number of pages7
    JournalChemical and Pharmaceutical Bulletin
    Volume38
    Issue number2
    DOIs
    Publication statusPublished - 1990

    All Science Journal Classification (ASJC) codes

    • Chemistry(all)
    • Drug Discovery

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