Work

Chlorocyclization of Alkenoic Thioester

Year: 2024

Type: article

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.

Source: Chemical and Pharmaceutical Bulletin

DOI: 10.1248/cpb.c24-00632

Authors: Miari Kurihara, Kanaru Sasaki, Hiroki Shigehisa

Institution: Musashino University

Language: English

Topic: Sulfur-Based Synthesis Techniques

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funder: Japan Society for the Promotion of Science

Award: MHAT／RPC化学の新展開