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Updated: Jun 6, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Chlorocyclization of Alkenoic Thioester
Miari Kurihara1, Kanaru Sasaki1, Hiroki Shigehisa1
1Department of Pharmacy, Musashino University.
Abstract:
This study introduces a novel method for ring-closing chlorosulfenylation of alkenoic thioesters using N-chlorosuccinimide in hexafluoroisopropanol under mild conditions. This reaction efficiently forms five-membered cyclic sulfur compounds with high selectivity, representing a significant advancement in the synthesis of chlorinated S-heterocycles. Computational analysis using density functional theory demonstrates the superiority of thioester nucleophiles over traditional benzyl sulfides in this reaction, highlighting the energetic preference for thioesters.
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