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Synthesis 1994; 1994(1): 34-36
DOI: 10.1055/s-1994-25399
short paper
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Tetrabutylammonium Fluoride: A Powerful Catalyst for the Regioselective Opening of Epoxides with Thiols

Domenico Albanese* , Dario Landini, Michele Penso
  • *Dipartimento di Chimica Organica e Industriale and Centro CNR Università di Milano, Via Golgi 19, I-20133 Milano, Italy
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Publication Date:
17 September 2002 (online)

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Tetrabutylammonium fluoride (1) catalyses under mild conditions the opening of epoxides 2a-k with thiols 3-6 to produce the corresponding ß-hydroxy thioethers 7-11 in excellent yields (88-100%) and with high regioselectivity. Furthermore, O-protected glycidols react without any loss of the protective group.