Isolation of the key intermediates in the catalyst-free conversion of oxiranes to thiiranes in water at ambient temperature

…, L Horst, C Würtele, R Wende, PR Schreiner

Index: Kleiner, Christian M.; Horst, Luise; Wuertele, Christian; Wende, Raffael; Schreiner, Peter R. Organic and Biomolecular Chemistry, 2009 , vol. 7, # 7 p. 1397 - 1403

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Citation Number: 10

Abstract

An early report on the synthesis and the proposed mechanism for thiirane formation was made by van Tamelen by using inorganic thiocyanate salts in aqueous and dilute alcoholic solutions. 5 This procedure is still the method of choice for epoxides with S N 2 reactivity. 12–14 Other possibilities for the preparation of thiiranes are the conversion of oxiranes with thiourea, 12,15–19 phosphine sulfides, 20 or dimethylthioformamide in the presence of ...