Categories: Synthesis of S-Heterocycles, C-S Bond Formation > Synthesis of Cyclic Sulfides >
Synthesis of thiiranes
A general, straightforward and odourless ring-opening reaction allows the preparation of β-hydroxy sulfides from in situ generated S-alkylisothiouronium salts in urea-choline chloride-based deep eutectic solvent (DES). The reaction of epoxides with thiourea in DES yields the corresponding thiiranes.
N. Azizi, Z. Yadollahy, A. Rahimzadeh-oskooee, Synlett, 2014, 25, 1085-1088.
Thiiranes are obtained in excellent yields and with high diastereoselectivity upon microwave irradiation of a mixture of α-haloketones, O,O-diethyl hydrogen phosphorodithioate and alumina-supported sodium borohydride in solvent-free conditions.
L. D. S. Yadav, R. Kapoor, Synthesis, 2002, 2344-2346.