Organocatalytic Synthesis of Thiiranes from Alkenes

Thiiranes, the corresponding sulfur analogues of epoxides, are considerably less analyzed and much less encountered in literature. This could possibly be owing to the minimal present synthetic techniques for their synthesis. Herein, a delicate, sustainable and economical organocatalytic synthesis of thiiranes has been developed. Setting up from olefins and employing the epoxidation protocol created in the Kokotos’ group, which employs 2,2,2-trifluoroacetophenone as the organocatalyst and H2O2 as the oxidant, followed by ring opening by thiourea, a wide range of thiiranes have been synthesized. Both fragrant and aliphatic moieties are perfectly tolerated, major to thiiranes in average to great yields.

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