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Synlett 1994; 1994(4): 267-268
DOI: 10.1055/s-1994-22822
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Fluoride Ion Promoted Synthesis of Thiiranes

Giuseppe Capozzi* , Stefano Menichetti, Simonetta Neri, Aleksandra Skowronska
  • *Centro C.N.R. "Chimica dei Composti Eterociclici", Dipartimento di Chimica Organica, Universita' di Firenze, Via G. Capponi 9, I-50121, Firenze, Italy
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Publication Date:
22 March 2002 (online)

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Thioxaphosphoranesulfenyl bromide 1 reacts with various aliphatic alkenes to give the corresponding adducts 3. These species can be reacted with tetrabutylammonium fluoride trihydrate (TBAF·3H2O) at room temperature to give the episulfides 4 in satisfactory yield. The great affinity of fluoride to phosphorus is claimed to be the driving force in the formation of the ß-bromo thiolate ion 6 which gives ring closure.

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