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A sulfonating ionic liquid for one-pot pseudo four-component synthesis of novel 3-chlorosulfonyl-δ-sultones: A novel class of fluorescent compounds

Author:
Toorchi Roudsari, Saeedeh, Rad-Moghadam, Kurosh
Source:
Tetrahedron 2018
ISSN:
0040-4020
Subject:
acetophenones, ambient temperature, catalysts, chemical reactions, chemical structure, condensates, fluorescence, fluorescent substances, ionic liquids, nuclear magnetic resonance spectroscopy, spectral analysis
Abstract:
An active imidazolium-based ionic liquid mixture was developed for efficient synthesis of some novel 4,6-diaryl-3-(chlorosulfonyl)-1,2-oxathiine-2,2-dioxides (chlorosulfonyl-δ-sultones) from simple acetophenones at room temperature. The ionic liquid mixture acts as a catalyst to condense two molecules of an acetophenone derivative and as a mild sulfonating agent to convert the resulting condensate into 4,6-diaryl-1,2-oxathiine-2,2-dioxides, and finally as a chlorosulfonating reagent to deliver the desired fully unsaturated chlorosulfonyl-δ-sultones in onepot. The products were separated easily from the reaction mixture and showed valuable fluorescence properties. The structures of these products are in good agreement with their ¹H NMR, ¹³C NMR, and mass spectral data. All rights reserved.
Agid:
6018079