Reaction for nucleophilic opening of thiirane ring by thiols

NMR and mass spectroscopic studies on n-(alkylthio)-1-alkanethiols

“…Most of the investigated n-(alkylthio)-1-alkanethiols 1 were newly synthesized. 2-(Alkylthio)-l-ethanethiols can 0021-8561/90/1438-0123$02.50/0 be obtained by several methods as reaction of 1,3-dithiolane derivatives with Ca/NH3 (Newman and Eliel, 1970) or of thiirane with alkyl mercaptans (Fokin et al, 1975;Meade and Woodward, 1948;Oswald, 1971Oswald, ,1979 or reaction of 2-(alkylthio) -1 -haloethanes with thiourea (Yarv et al, 1976). The latter reaction of n-(alkylthio)-!haloalkanes (Anklam, 1987; Palmer and Taylor, 1986) with thiourea is most useful for syntheses of all compounds with > 2.…”

Ionic Liquids-Assisted Ring Opening of Three-Membered Heterocycles with Thio- and Seleno-Silanes

“…Several methods dealing with the reaction of thiiranes with thiols or thiolates to obtain mercapto sulfides through a S N 2 ring opening reaction in the presence of suitable catalysts have been reported. It has been observed that the product's distribution pattern depends on the reaction conditions, such as the type of the nucleophile, the solvent polarity, the concentration, and the reaction temperature [74,75].…”

Small heterocyclics as hydrogen bond acceptors and donors: the case of the C2H3XS···NH3 complexes (X = H, F and CH3)

“…Thiirane (C 2 H 4 S), in particular, is a three-member heteroring possessing properties internally related to nucleophilic reaction mechanisms [4]. In order to understand the functionality of C 2 H 4 S in nucleophilic reactions, one of the most widely used courses of investigation is the characterization of transition state based on interaction between C 2 H 4 S and a number of well-known nucleophiles [5], such as ammonia (NH 3 ).…”