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Synlett 1999; 1999(11): 1739-1742
DOI: 10.1055/s-1999-2934
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The First Synthesis of α,β-Acetylenic Thioketones and Thioaldehydes

Alessandro Degl'Innocenti* , Antonella Capperucci, Patrizia Scafato, Tommaso Mecca, Gianna Reginato, Alessandro Mordini
  • *Centro C.N.R. Composti Eterociclici, c/o Dipartimento di Chimica Organica, via G. Capponi 9, 50100 Firenze, Italy; Fax +39 0 55 2 47 69 64; E-mail: degli@chimorg.unifi.it
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Publication History

Publication Date:
31 December 1999 (online)

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Reaction of several β-silyl acetylenic ketones with hexamethyldisilathiane (HMDST) in the presence of TfOTMS affords a simple and direct entry to silylated acetylenic thioketones and, after desilylation, to the corresponding unsubstituted α,β-unsaturated thioketones. The procedure similarly affords the first synthesis of an acetylenic thioaldehyde.

alkynes - cycloadditions - silicon - thionation - thiocarbonyl

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